Tag: M.W=200-300

Application of 171011-37-3, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 171011-37-3, name is (4-Bromo-1,2-phenylene)dimethanol. A new synthetic method of this compound is introduced below.

Step 2: Synthesis of (5-bromo-2-(chloromethyl)phenyl)methanol A flask was charged with (4-bromo-1,2-phenylene)dimethanol (4.00 g, 18.4 mmol, 1.00 equiv) and hydrochloric acid (25 mL). The resulting solution was stirred for 15 min at 70 C and quenched with water (50 mL). The mixture was extracted with EtOAc (2 x 80 mL) and the organic layers were combined, dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was chromatographed on a silica gel column with EtOAc/petroleum ether (1/8) to provide 2.70 g (62% yield) of (5-bromo-2-(chloromethyl)phenyl)methanol as an off-white solid.1H NMR (300 MHz, DMSO-d6) ^ 7.64- 7.66 (m, 1H), 7.45- 7.49 (m, 1H), 7.36 (d, J = 8.1 Hz, 1H), 5.40- 5.45 (m, 1H), 4.78 (s, 2H), 4.66 (d, J = 4.5 Hz, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,171011-37-3, (4-Bromo-1,2-phenylene)dimethanol, and friends who are interested can also refer to it.

Reference:
Patent; ABIDE THERAPEUTICS, INC.; BUZARD, Daniel J.; SHAGHAFI, Michael B.; CISAR, Justin S.; GRICE, Cheryl A.; JONES, Todd K.; WEBER, Olivia D.; (277 pag.)WO2017/197192; (2017); A1;,
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Reference of 575-03-1, Adding some certain compound to certain chemical reactions, such as: 575-03-1, name is 7-Hydroxy-4-(trifluoromethyl)coumarin,molecular formula is C10H5F3O3, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 575-03-1.

General procedure: The appropriate bromoketone (6a-o) (1.7 mmol) and triethylamine (1.6 mmol) were added to as olution of either7-hydroxy-4-methyl-2H-chromen-2-one 4 (1.4 mmol)or 7-hydroxy-4-(trifluoromethyl)-2H-chromen-2-one 5 (1.4 mmol) in THF (20 mL). The mixture was stirred at room temperature for 24h, filtered and the solvent was evaporated under reduced pressure.The solid residue was purified by column chromatography eluting with DCM/MeOH 9:1 to afford (7a-n) and (8a-o).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 575-03-1, 7-Hydroxy-4-(trifluoromethyl)coumarin, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kandil, Sahar; Westwell, Andrew D.; Mcguigan, Christopher; Bioorganic and Medicinal Chemistry Letters; vol. 26; 8; (2016); p. 2000 – 2004;,
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Application of 5391-88-8, Adding some certain compound to certain chemical reactions, such as: 5391-88-8, name is 1-(4-Bromophenyl)ethanol,molecular formula is C8H9BrO, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 5391-88-8.

l-(4-bromo-phenyl)-ethanol is stirred in aq. HCl at room temperature for 20 h. The excess acid is evaporated under vacuum to give the expected product in quantative yield.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 5391-88-8, 1-(4-Bromophenyl)ethanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GALAPAGOS NV; MENET, Christel Jeanne Marie; BLANC, Javier; JOUANNIGOT, Nolwenn; HODGES, Alastair James; VAN ROMPAEY, Luc Juliaan Corina; FLETCHER, Stephen Robert; WO2010/10189; (2010); A1;,
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Electric Literature of 2615-15-8, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 2615-15-8 as follows.

1005671 A solution of hexaethylene glycol (10 g, 35.46 mmol) in DCM (100 mL) was charged with Ag20 (12.34 g, 53.19 mmol), KI (1.17 g, 7.04 mmol) and stirred at room temperature for 15 mm. This solution was charged with tosyl chloride (7.35 g, 38.68 mmol)and stirred at room temperature for 6 h. The reaction mixture was filtered through a pad of celite and the filtrate was concentrated in vacuo resulting in a crude compound which was purified by chromatography on silica gel, eluting with 2% methanol in DCM to give 8.80 g, 57% yield of the title compound as colorless oil. ?H NMR (400 MHz, DMSO-d6): oe = 7.78 (d, J= 7.9 Hz, 2H), 7.48 (d, J= 7.7 Hz, 2H), 4.56 (t, J= 5.4 Hz, 1H), 4.11 (t, J= 4.3 Hz, 2H), 3.563.32 (m, 22H), 2.42 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,2615-15-8, its application will become more common.

Reference:
Patent; COFERON, INC.; FOREMAN, Kenneth, W.; JIN, Meizhong; WANNER, Jutta; WERNER, Douglas, S.; WO2015/106292; (2015); A1;,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 25574-11-2, name is 3-(4-Bromophenyl)propan-1-ol, the common compound, a new synthetic route is introduced below. HPLC of Formula: C9H11BrO

(41-3) Synthesis of 4-bromo-1-(3-bromopropyl)benzene (compound 41-3) Compound 41-2 (3.63 g) was dissolved in methylene chloride (40 ml), triphenylphosphine (4.88 g) and N-bromosuccinimide (3.31 g) were added under ice-cooling, and the mixture was stirred under ice-cooling for 2 hr, and at room temperature for 4 hr. The reaction mixture was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. Diethyl ether (100 ml) was added, and the precipitated triphenylphosphine oxide was filtered off. The concentrate of the filtrate was purified by silica gel column chromatography (hexane alone) to give the object product (1.87 g) as a colorless oil. 1H-NMR(CDCl3) delta (ppm): 2.10-2.17(2H, m), 2.74(2H, t, J=7.4Hz), 3.38(2H, t, J=6.5Hz), 7.08(2H, d, J=8.3Hz), 7.41(2H, dd, J=8.3, 1.9Hz).

The synthetic route of 25574-11-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Mitsubishi Tanabe Pharma Corporation; EP2168944; (2010); A1;,
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Related Products of 83647-43-2, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 83647-43-2 as follows.

Step B. The intermediate from Step A above (18.1 g) was dissolved in anhydrous CH2Cl2 (150 mL) under nitrogen and the reaction vessel was cooled to 00C in an ice bath. To this cooled solution was added PBr3 (5.52 mL) over a 10 min period. Once the addition was complete, the reaction mixture was warmed to room temperature and stirred for an additional 12 h. The mixture was cooled in an ice bath and quenched by the dropwise addition of MeOH (20 mL). The organic phase was washed with saturated NaHCO3 (2 x 150 mL), dried over anhydrous MgSO4, filtered, and then concentrated to afford the intermediate (23.8 g; 97 %) as viscous oil. 1H-NMR (CDCl3) delta = 2.50 (s, 3 H), 4.50 (s, 2 H), 7.00 (t, H), 7.25 (d, 1 H), 7.50 (d, 1 H). Step B. Under a nitrogen atmosphere PBr3 (5.52 mL) was added over a lO min period to an ice cooled solution of the title compound from Step A above (18.1 g) in anhydrous CH2Cl2 (15O mL). The cooling bath was removed and mixture stirred at room temperature for 12 h. The mixture was cooled (0-5C), quenched by dropwise addition of MeOH (20 mL), washed with saturated aqueous NaHCO3 (2 x 15O mL), dried (MgSO4), filtered and concentrated to afford the title compound as a viscous oil (23.8 g, 97%). 1H-NMR (CDCl3) delta = 7.50 (d, 1 H), 7.25 (d, 1 H), 7.00 (t, 1 H), 4.50 (s, 2 H), 2.50 (s, 3 H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,83647-43-2, its application will become more common.

Reference:
Patent; ALANTOS PHARMACEUTICALS HOLDING, INC.; WO2008/63671; (2008); A2;,
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Reference of 722-92-9 , The common heterocyclic compound, 722-92-9, name is 2-(4-Aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol, molecular formula is C9H7F6NO, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

Step 10: tert-Butyl 1-{[4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl]carbamoyl}-5-(methylsulfamoyl)-1,3-dihydro-2H-isoindole-2-carboxylate (0505) (0506) 2-(4-Aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (2.84 g, 10.94 mmol) was added to a mixture of 2-(tert-butoxycarbonyl)-5-(N-methylsulfamoyl)isoindoline-1-carboxylic acid (3 g, 8.42 mmol), HATU (4.16 g, 10.94 mmol) and DIPEA (2.94 mL, 16.84 mmol) in DCM (50 mL) under nitrogen. The resulting mixture was stirred at room temperature for 2 hours. The reaction mixture was quenched with saturated NH4Cl (75 mL), extracted with DCM (3×75 mL), the organic layer was dried over Na2SO4, filtered and evaporated to afford orange solid. The crude product was purified by flash silica chromatography, elution gradient 30 to 50percent EtOAc in petroleum ether. Pure fractions were evaporated to dryness to afford tert-butyl 1-((4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl)carbamoyl)-5-(N-methylsulfamoyl)isoindoline-2-carboxylate (3.00 g, 59.6percent) as a yellow solid. (0507) LC/MS: m/z=598 [M+H]+. 1H NMR (300 MHz, DMSO-d6, mixture of rotamers, 1.8*:1) delta 1.36*, 1.48 (s, 9H), 2.43 (d, 3H), 4.63-4.87 (m, 2H), 5.60-5.77 (m, 1H), 7.49-7.85 (m, 8H), 8.66*, 8.67 (s, 1H), 10.75 (s, 1H).

The synthetic route of 722-92-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AstraZeneca AB; NARJES, Frank; OLSSON, Roine Ingemar; VON BERG, Stefan; LEVER, Sarah; (112 pag.)US2017/166527; (2017); A1;,
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Electric Literature of 101597-25-5, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.101597-25-5, name is 1,1-Bis(4-methoxyphenyl)prop-2-yn-1-ol, molecular formula is C17H16O3, molecular weight is 268.31, as common compound, the synthetic route is as follows.

Comparative Example 1 3,3-Dianisyl-3H-naphtho[2,1-b]pyran. A mixture of 2-naphthol (3.23 g;0.0224 mol), 1,1-dianisylprop-2-yn-1-ol (6.00 g;0.0224 mol), acidic alumina Brockmann 1(6 g) and toluene (250 ml) was heated and stirred for 1.5 h, cooled, filtered and the solid washed with toluene. The filtrate was evaporated to give a pale purple tacky solid which was washed with pet. ether (40-60)/diethyl ether to yield crude product (7.07 g). Purification of the solid by crystallisation from ethylacetate gave 3,3-dianisyl-3H-naphtho[2,1-b]pyran as a white solid (5.52 g;66% yield), m.pt 176-177 C. STR10

The chemical industry reduces the impact on the environment during synthesis 101597-25-5, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Pilkington PLC; US5520853; (1996); A;,
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Electric Literature of 575-03-1, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 575-03-1, name is 7-Hydroxy-4-(trifluoromethyl)coumarin. A new synthetic method of this compound is introduced below.

General procedure: The appropriate bromoketone (6a-o) (1.7 mmol) and triethylamine (1.6 mmol) were added to as olution of either7-hydroxy-4-methyl-2H-chromen-2-one 4 (1.4 mmol)or 7-hydroxy-4-(trifluoromethyl)-2H-chromen-2-one 5 (1.4 mmol) in THF (20 mL). The mixture was stirred at room temperature for 24h, filtered and the solvent was evaporated under reduced pressure.The solid residue was purified by column chromatography eluting with DCM/MeOH 9:1 to afford (7a-n) and (8a-o).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,575-03-1, 7-Hydroxy-4-(trifluoromethyl)coumarin, and friends who are interested can also refer to it.

Reference:
Article; Kandil, Sahar; Westwell, Andrew D.; Mcguigan, Christopher; Bioorganic and Medicinal Chemistry Letters; vol. 26; 8; (2016); p. 2000 – 2004;,
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Application of 722-92-9 ,Some common heterocyclic compound, 722-92-9, molecular formula is C9H7F6NO, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

Intermcdiate H; 6-Chloro-3-(2-ethoxy-3,4-dioxo-cyclobut- 1 -enylamtno)-2-hydroxy-N-(4-{2,2,2-trif luoro-1 – hydroxy-l-triftuoromepsilonthyl-ethyl)-phenylj-benzenesulfonamide; HIi Preparation of Intermediate Ht; 2-rert-Butyl-6-chloro-ben*zooxazole-7-sul-:onic acid [4-{2,2,2-trifluoro-l -hydroxy-1 -trifluoromethyl-ethy I )~rhohenyl]-amide; 2-tert-Buryl-6-chJoro-ben20oxazole-7-sulfonyl chloride (500 mg, 1.62 mmo.) {prepared according to the procedure described in US 2007/067088 page 17} , 2-(4-aminophenyl)- l,l,l,3,3,3-hexafluoropropan-2-ol (420 mg, 1.62 mmol) and triethylamine (0.226 ml, 1.62 mmol) were combined in THF (5 ml) to give a yellow solution. The reaction, mixture was stirred at room temperature for 2 h then heated at 50 0C for 48 h. The reaction mixture was partitioned between EtOAc (20 ml) and IM HCI (10 ml), live organic layer was washed with brine (10 ml), dried (MgSO-O, filtered and added to silica gel (4 g) then carefully evaporated in vacuo. The silica gel was dry-loaded onto an (Isolure.(TM). Flash Si II 25 g) column for purification by chromatography, eluting with iso-hexane/ErOAc (10/1). The product fractions were combined and evaporated to dryness in vacuo to yield the title product. IH NMR 6H (400MHz DMSO) 8.55 (s, IH), 7.94 (d, IH), 7.61 (d, IH), 7.49 (d, 2H) 7.19 Patent; NOVARTIS AG; BAETTIG, Urs; BRUCE, Ian; PRESS, Neil John; WATSON, Simon James; WO2010/63802; (2010); A1;,
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