3-Methyl-5-(trifluoromethyl)benzoic acid → (3-Methyl-5-(trifluoromethyl)phenyl)methanol

To a stirred suspension of 3-methyl-5-(trifluoromethyl)benzoic acid (1 g, 4.90 mmol) in THF (5 ml) at −78° C. under nitrogen was added dropwise over 10 mins borane tetrahydrofuran complex 1M in THF (24.49 ml, 24.49 mmol). The reaction mixture was then allowed to warm to RT over 20 hours. On cooling in an ice/water bath the reaction mixture was quenched dropwise with MeOH (10 ml) and then 1M HCl until effervescence ceased. Water was added and the reaction mixture stirred at RT for 30 mins and the THF was removed under reduced pressure. EtOAc was added and the organic portion 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. temperatureOn cooling in an ice/water bath the reaction mixture
2. customwas quenched dropwise with MeOH (10 ml)
3. additionWater was added
4. customthe THF was removed under reduced pressure
5. additionEtOAc was added
6. dry with materialthe organic portion dried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. customPurification

ORD record

ord-f4e618062bf64f738d72d6f8d743b592

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09409895B2