Sodium → (5-Bromo-2-chloro-phenyl)-[4-(trifluoromethoxy)phenyl]methanol

Temperature

0 °C

To the solution of (5-bromo-2-chloro-phenyl)-[4-(trifluoromethoxy)phenyl]methanone 15e (5.0 g, 13.0 mmol) in a dry tetrahydrofuran/methanol mixture (v/v=1/1, 20 mL) was added sodium brohydride (0.98 g, 26.0 mmol) in portions at 0° C. After the addition, the mixture was stirred at 0° C. for 40 min. The reaction mixture was quenched with water (5 mL) and extracted with ethyl acetate (50 mL). The water layer was extracted with ethyl acetate (30 mL×2). The combined organic layers were washed with saturated brine (30 mL×2), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to give the title compound 15f as pale yellow oil (5.0 g, 99.5%). This material was not further purified.

1. additionAfter the addition
2. customThe reaction mixture was quenched with water (5 mL)
3. extractionextracted with ethyl acetate (50 mL)
4. extractionThe water layer was extracted with ethyl acetate (30 mL×2)
5. washThe combined organic layers were washed with saturated brine (30 mL×2)
6. dry with materialdried over anhydrous sodium sulfate
7. filtrationfiltered
8. concentrationThe filtrate was concentrated in vacuo

ORD record

ord-20269d73960e4f6b956bf7162cd0233e

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09394329B2