反应详情

To a solution of 3,5-difluoro-4-(methylthio)-benzaldehyde (31.3 g, 0.166 mol) in anhydrous THF (200 mL) cooled with a cold water bath was added sodium borohydride (1.6 g, 0.042 mol) in portions over 30 minutes. After stirring 1 hour at room temperature, excess dilute HCl was added, until gas evolution ceased. Water (600 mL) was added and the mixture extracted with dichloromethane (1×500 mL, 1×100 mL). The combined extracts were washed once with water, dried with magnesium sulfate, and concentrated. Purification by silica gel chromatography using 3% ethyl acetate/10% dichloromethane in hexanes initially, and eluting product with 60% ethyl acetate in hexanes gave [3,5-difluoro-4-(methylthio)-phenyl]methanol as a light yellow liquid (24.8 g, 78%). 1H NMR (CDCl3/400 MHz) 6.88-6.93 (m, 2H), 4.65 (s, 2H), 2.42 (s, 3H). HRMS m/z 190.0266 (M+H+, calcd 190.0264).

1. extractionthe mixture extracted with dichloromethane (1×500 mL, 1×100 mL)
2. washThe combined extracts were washed once with water
3. dry with materialdried with magnesium sulfate
4. concentrationconcentrated
5. customPurification by silica gel chromatography
6. washeluting product with 60% ethyl acetate in hexanes