Methanol → (3,5-Difluoro-2-methoxy-phenyl)-methanol

To an ice-cold solution of 1.7 g (9.03 mmol) of 3,5-difluoro-2-methoxy-benzaldehyde in 10 ml of dry tetrahydrofuran was added under an argon atmosphere 1 ml of borane dimethylsulfide complex. The reaction mixture was warmed up and stirred for 24 hours at room temperature. Thereupon, the mixture was again cooled to 0° C. and 5 ml of methanol were added dropwise within 30 minutes. Subsequently, the solvent was distilled and the crude product was purified by chromatography on silica gel with a 1:1 mixture of diethylether and dichloromethane as the eluent. There were obtained 0.89 g (56% of theory) of (3,5-difluoro-2-methoxy-phenyl)-methanol as a colorless liquid; MS: 174 (M)+.

1. temperatureThe reaction mixture was warmed up
2. temperatureThereupon, the mixture was again cooled to 0° C.
3. distillationSubsequently, the solvent was distilled
4. customthe crude product was purified by chromatography on silica gel with a 1:1 mixture of diethylether and dichloromethane as the eluent

ORD record

ord-40c4faa6044f4d74959665093d97d6b7

Source dataset

uspto-grants-2002_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06376672B1