Electric Literature of 7073-69-0 ,Some common heterocyclic compound, 7073-69-0, molecular formula is C9H11BrO, 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.
To a solution of n-BuLi (166 mL, 2.6 M, 432 mmol) in 200 mL of THF at -78 C. under argon was slowly added a solution of Compound 10d (42.2 g, 196 mmol) in 60 mL of THF at a rate that the internal temperature remained below -70 C. The mixture was stirred at -75 C. for 2 h. To the reaction mixture was then added triisopropylborate (59 mL, 255 mmol) in three portions. The mixture was allowed to warm slowly to room temperature overnight. The mixture was then cooled to 0 C., and was carefully quenched with dilute hydrochloric acid (250 mL, 2N). The mixture was then stirred at room temperature for 1 h. The pH of the mixture was checked and adjusted to acidic using additional 2N HCl if prophetic. The two layers were separated, and the aqueous layer was extracted twice with ether. The organic layers were combined, and dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to yield a pale yellow oil. The residue was then diluted with ethyl acetate (400 mL) and, washed with 1N sodium hydroxide solution (150 mL×3). The basic aqueous layers were combined and acidified with 2N HCl. The clear solution turned cloudy when the acid was added. The mixture was extracted with ether (150 mL×3). The organic layers were combined and dried with magnesium sulfate. The solution was filtered, and the filtrate was concentrated under reduced pressure to yield the title Compound 10e as a colorless oil (26.2 g, 82%) which was used without further purification in the next step. 1H NMR (400 MHz, DMSO-d6) delta (ppm): 9.00 (s,1H), 7.66 (dm,1H, J=7.3 Hz), 7.45 (dt, 1H, J=1.1, 7.7 Hz), 7.40 (dm, 1H, J=7.6 Hz), 7.31 (dt, 1H, J=1.2, 7.1 Hz), 1.44 (s, 6H).
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. 7073-69-0, 2-(2-Bromophenyl)propan-2-ol, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; Player, Mark R.; Dax, Scott L.; Parsons, William H.; Brandt, Michael Richard; Calvo, Raul R.; Patel, Sharmila; Liu, Jian; Cheung, Wing S.; Jetter, Michele C.; Lee, Yu-Kai; Youngman, Mark A.; Pan, Wenxi; Weils, Kenneth M.; Beauchamp, Derek A.; US2007/259936; (2007); A1;,
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