Related Products of 7073-69-0, 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. 7073-69-0, name is 2-(2-Bromophenyl)propan-2-ol. A new synthetic method of this compound is introduced below.
A flask under nitrogen was charged with vinyl alcohol IV (97 g), bromo alcohol IIA (81g ), DMF (380 mL) and N,N-dicyclohexylmethylamine (Cy2NMe, 96.5 mL). To the reaction mixture was charged tri-o-tolylphosphine ((o-tol)3P, 506 mg) and trans-diaminedibromopalladium(II) ((NH3)2PdBr2> 454 mg). The batch was heated to 100 C and aged until completion. To the batch was charged 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU, 68.3 mL). The mixture was heated to 120C and aged for at least 6h. The batch was cooled to 45C, aq. Glycolic acid (56.8 mL, 70 wt %,) was slowly charged. Oxoalcohol VA was crystallized by slow addition of anti-solvent DI water at 55C. The crystalline product was dried at room temperature under vacuum with nitrogen sweep to yield oxoalcohol VA (110.7 g, 82% corrected yield from the vinyl alcohol IV. 1NMR (500MHz, CDCl3) delta 8.25 (m, 1H), 8.11 (d, J= 8.5 Hz, 1H), 8.08 (d, J= 1.5 Hz, 1H), 7.94 (m, 1H), 7.80 (m, 1H), 7.75 (d, J- 17.5 Hz, 1H), 7.72 (d, J= 5.0 Hz, 1H), 7.62 (d, J= 8.5 Hz, 1H), 7.49 (m, 1H), 7.46 (dd, J= 8.6, 2.0 Hz 1H), 7.43 (om, 1H), 7.42 (d, J= 16.3 Hz, 1H), 7.29 (dd, J= 7.6, 1.7 Hz, 1H), 7.24 (m, 1H), 7.19 (m, 1H), 3.49-3.42 (om, 4H), 2.47 (s, 1H), 1.73 (s, 6H). 13C NMR (125MHz, CDCl3) delta 199.7, 156.4, 148.6, 145.6, 139.8, 137.4, 136.8, 136.2, 135.6, 134.0, 131.6, 131.5, 129.6, 129.1, 128.7, 128.24, 128.21, 127.28, 127.26, 126.8, 126.0, 125.75, 125.69, 119.8, 73.8, 42.0, 32.2, 28.5. LC-MS (ESI+) m/z calculated C29H27C1N02 for 456.2 found 456.5 (M+H).
At the same time, in my other blogs, there are other synthetic methods of this type of compound,7073-69-0, 2-(2-Bromophenyl)propan-2-ol, and friends who are interested can also refer to it.
Reference:
Patent; MERCK SHARP & DOHME CORP.; ALBANEZE-WALKER, Jennifer, E.; CHEN, Yonggang; HUMPHREY, Guy; KRSKA, Shane William; QI, Ji; TAN, Lushi; ITOH, Tetsuji; FUNANE, Shigeru; YOKOZAWA, Tohru; KOBAYASHI, Tohru; WO2014/81616; (2014); A1;,
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