Hydride → (3-Chloro-5-(trifluoromethyl)phenyl)methanol

To a stirred solution of methyl 3-chloro-5-(trifluoromethyl)benzoate (Reference Example 29, 2.20 g, 9.22 mmol) in THF (100.0 mL) at −78° C. was added disobutylaluminum hydride solution (28.00 mL, 1.0 M in methylene chloride, 28.00 mmol) and the resulting reaction mixture was stirred at this temperature for 4 h. After this time, the reaction was quenched with 1.0 M hydrochloric acid (100 mL) and warmed to room temperature. The reaction mixture was diluted with ethyl acetate, washed with aqueous 1.0 M hydrochloric acid, water, and saturated sodium chloride, dried (Na2SO4), filtered, concentrated under reduced pressure to provide (3-chloro-5-(trifluoromethyl)phenyl)methanol (1.98 g, >99%) as a brown oil, which was used without further purification or characterization.

1. customthe resulting reaction mixture
2. customAfter this time, the reaction was quenched with 1.0 M hydrochloric acid (100 mL)
3. additionThe reaction mixture was diluted with ethyl acetate
4. washwashed with aqueous 1.0 M hydrochloric acid, water, and saturated sodium chloride
5. dry with materialdried (Na2SO4)
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure

ORD record

ord-cb78efaa19254d6baa7b88449fb720a0

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08853215B2