3-Bromo-5-(trifluoromethyl)benzoic acid → [3-Bromo-5-(trifluoromethyl)phenyl]methanol

To a stirred solution of 3-bromo-5-(trifluoromethyl)benzoic acid (1 g, 3.72 mmol) in THF (5 ml) at −78° C. with stirring under nitrogen was added dropwise over 10 mins borane tetrahydrofuran complex 1M in THF (18.59 ml, 18.59 mmol) and then the reaction mixture was warmed to RT over 20 hours. The reaction mixture was cooled in an ice/water bath and quenched dropwise with MeOH (10 ml) followed by 1M HCl until effervescence ceased. Water was added and stirred at RT for 30 mins. THF was removed under reduced pressure, and the compound extracted into EtOAc. The organic portion was dried over MgSO4, filtered and concentrated under reduced pressure. Purification was carried out by chromatography on silica using 0-50% EtOAc in Hexanes as eluent to afford the title product.

1. temperatureThe reaction mixture was cooled in an ice/water bath
2. customquenched dropwise with MeOH (10 ml)
3. additionWater was added
4. customTHF was removed under reduced pressure
5. extractionthe compound extracted into EtOAc
6. dry with materialThe organic portion was dried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. customPurification

ORD record

ord-2bafdf9c025d4e3bb15e6a9f4c395e29

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09409895B2