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

Temperature

0 °C

(5-bromo-2-chloro-phenyl)-[4-(trifluoromethoxy)phenyl]methanone 6f (4.35 g, 11.5 mmol) was dissolved in 40 mL of mixed solution (THF and MeOH, v:v=1:1) and cooled to 0° C., followed by addition of sodium borohydride (0.87 g, 23.0 mmol) in batch. The reaction mixture was stirred for 30 minutes at 0° C. Thereafter, the reaction mixture was concentrated under reduced pressure after 10 mL acetone were added. The reaction mixture was partitioned after 100 mL ethyl acetate and 50 mL water were added and the organic extract was washed with saturated sodium chloride solution (50 mL×2), combined, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure to obtain the title compound (5-bromo-2-chloro-phenyl)-[4-(trifluoromethoxy)phenyl]methanol 6g (4.4 g, pale yellow grease), which was used directly in the next step without purification. 1H NMR (400 MHz, CDCl3): δ 7.80 (d, 1H), 7.43-7.40 (m, 2H), 7.36 (dd, 1H), 7.20 (t, 3H), 6.16 (s, 1H).

1. concentrationThereafter, the reaction mixture was concentrated under reduced pressure after 10 mL acetone
2. additionwere added
3. customThe reaction mixture was partitioned after 100 mL ethyl acetate and 50 mL water
4. additionwere added
5. extractionthe organic extract
6. washwas washed with saturated sodium chloride solution (50 mL×2)
7. dry with materialdried over anhydrous magnesium sulfate
8. filtrationfiltered
9. concentrationThe filtrate was concentrated under reduced pressure

ORD record

ord-844d286d0926485d8bfcf71a1ba4f8b5

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08609622B2