3-Chloro-5-(trifluoromethyl)benzaldehyde → 1-(3-Chloro-5-(trifluoromethyl)phenyl)ethanol

To a stirred solution at −10° C. of 3-chloro-5-(trifluoromethyl)benzaldehyde (Reference Example 31, 1.15 g, 5.51 mmol) in THF (20.0 mL) was added dropwise methyl magnesium bromide (2.30 mL, 3.0 M in ethyl ether, 6.90 mmol). After the addition was complete, the reaction mixture was stirred for an additional 1.5 h, then the reaction was quenched with saturated ammonium hydrochloride (30.0 mL), and the mixture was warmed to room temperature. The reaction mixture was diluted with ethyl acetate, washed with water, and saturated sodium chloride, dried (Na2SO4), filtered and concentrated under reduced pressure to provide 1-(3-chloro-5-(trifluoromethyl)phenyl)ethanol (1.17 g, 94%) as a pale yellow oil, which was used without further purification or characterization.

1. additionAfter the addition
2. customthe reaction was quenched with saturated ammonium hydrochloride (30.0 mL)
3. additionThe reaction mixture was diluted with ethyl acetate
4. washwashed with water, and saturated sodium chloride
5. dry with materialdried (Na2SO4)
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure

ORD record

ord-3bb92f16ef9a41d4a96ffda93042ab6e

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08853215B2