Category: 149965-40-2

Electric Literature of 149965-40-2 , The common heterocyclic compound, 149965-40-2, name is (5-Bromo-2-chlorophenyl)methanol, molecular formula is C7H6BrClO, 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 1: 5-Bromo-2-chlorobenzaldehyde. To a suspension of 5.23 g (23.6 mmol) of 5-bromo-2-chlorobenzyl alcohol in 50 ml of CH2Cl2 at 0 C., 8.36 g (38.7 mmol) of pyridinium chlorochromate was added. The reaction mixture was stirred at room temperature for 3 hours at which time the reaction was complete. The mixture was filtered, washed with EtOAc, dried (MgSO4), filtered, and concentrated. Flash column chromatography (10% EtOAc/hexane) yielded a pale yellow solid (4.62 g, 89%): m.p. 56-58 C.: Rf 0.73 (20% EtOAc/hexane). 1H NMR (400 MHz, CDCl3) delta7.34 (d, J=8.4 Hz, 1, ArH), 7.65 (dd, J=8.4, 2.4 Hz, 1, ArH), 8.04 (d, J=2.4 Hz, 1, ArH), 10.41 ppm (s, 1, CHO).

The synthetic route of 149965-40-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dawson, Marcia J.; Fontana, Joseph A.; Zhang, Xiao-kun; Leid, Mark; Jong, Ling; Hobbs, Peter D.; US2003/176506; (2003); A1;,
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Electric Literature of 149965-40-2, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 149965-40-2, name is (5-Bromo-2-chlorophenyl)methanol. This compound has unique chemical properties. The synthetic route is as follows.

(5-Bromo-2-chloro-benzyloxy)-tert-butyl-dimethyl-silane TBDMS-Cl (10.6 g, 66.7 mmol) was added to a sol. of (5-bromo-2-chloro-phenyl)-methanol (12.8 g, 55.6 mmol) and imidazole (9.42 g, 138 mmol) in DMF (190 mL) at 0 C. The mixture was stirred for 2 h at 0 C., and aq. sat. NH4Cl was added. The mixture was extracted with heptane (2*). The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (heptane?EtOAc/heptane 1:49) yielded the title compound (18.0 g, 96%). LC-MS: tR=1.22 min.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 149965-40-2, (5-Bromo-2-chlorophenyl)methanol.

Reference:
Patent; Bezencon, Olivier; Bur, Daniel; Corminboeuf, Olivier; Dube, Daniel; Grisostomi, Corinna; MacDonald, Dwight; McKay, Dan; Powell, David; Remen, Lubos; Richard-Bildstein, Sylvia; Scheigetz, John; Therien, Michel; Weller, Thomas; US2009/176823; (2009); A1;,
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Application of 149965-40-2, Adding some certain compound to certain chemical reactions, such as: 149965-40-2, name is (5-Bromo-2-chlorophenyl)methanol,molecular formula is C7H6BrClO, 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 149965-40-2.

5-Bromo-2-chlorophenyl)methanol (15.0 g, 67.7 mmol), 4,4,4?,4?,5,5,5?,5?-octamethyl-2,2?-bi(1,3,2-dioxaborolane) (27.5 g, 108 mmol), KOAc (19.9 g, 203 mmol), and 1,4-dioxane (100 mL) were added to a 250 mL round-bottomed flask under N2. The mixture was sparged with N2 for 5 minutes and then treated with Pd(dppf)Cl2.CH2Cl2 (4.96 g, 6.07 mmol). The mixture was sparged with N2 for another 5 minutes and then stirred at 100 C. for 16 hours before cooling to room-temperature. The resultant mixture was filtered, and the filtrate was concentrated to dryness under reduced pressure to afford the product, which was purified by preparative HPLC (eluent: CH3CN/H2O and H2O with 0.04% NH3, 1:5 to 1:1, gradient elution) to afford pure product. The product was suspended in water (10 mL), the mixture frozen using dry ice/acetone, and then lyophilized to dryness to afford the title product (6.8 g) as a white solid. The white solid (6.8 g) was further purified by FCC (eluent:petroleum ether/ethyl acetate, 20:1 to 0:1) to afford the title compound (4.0 g, 22%). MS (ESI): mass calcd. for C13H18BClO3 268.1 m/z, found 251.0 [M-H2O+H]+. 1H NMR (400 MHz, CDCl3) delta 7.88 (s, 1H), 7.68-7.63 (m, 1H), 7.35 (d, J=7.9 Hz, 1H), 4.77 (d, J=6.4 Hz, 2H), 1.90 (t, J=6.6 Hz, 1H), 1.33 (s, 12H).

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. 149965-40-2, (5-Bromo-2-chlorophenyl)methanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Janssen Pharmaceutica NV; Barbay, J. Kent; Chai, Wenying; Hirst, Gavin C.; Kreutter, Kevin D.; Kummer, David A.; McClure, Kelly J.; Nishimura, Rachel T.; Shih, Amy Y.; Venable, Jennifer D.; Venkatesan, Hariharan; Wei, Jianmei; (501 pag.)US2020/55874; (2020); A1;,
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