4-Bromo-3-fluorobenzaldehyde → 1-(4-Bromo-3-fluorophenyl)ethan-1-ol

Methylmagnesium bromide (3M in diethylether, 6.77 mL, 20.31 mmol) was added dropwise over ˜15 min to a solution of 4-bromo-3-fluorobenzaldehyde (3.1 g, 15.27 mmol) in THF (50 mL) under argon at a temperature of −60° C. to −50° C. The ice bath was removed and the reaction mixture was allowed to warm to room temperature and stirred ˜20 hr. The reaction mixture was slowly diluted/quenched with saturated aqueous ammonium chloride solution (20 mL) and further diluted with water (10 mL). The separated aqueous layer was extracted with ethyl acetate (2×40 mL). The combined organic layers were washed with brine (60 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure to provide crude 1-(4-bromo-3-fluorophenyl)ethanol as a pale yellow oil, which was directly used without further purification.

1. customThe ice bath was removed
2. customThe reaction mixture was slowly diluted/quenched with saturated aqueous ammonium chloride solution (20 mL)
3. additionfurther diluted with water (10 mL)
4. extractionThe separated aqueous layer was extracted with ethyl acetate (2×40 mL)
5. washThe combined organic layers were washed with brine (60 mL)
6. dry with materialdried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure

ORD-Eintrag

ord-7c6b01ce93e14c73ba9a5c6e4f2dc85a

Quelldatensatz

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09434719B2