Sodium borohydride → (2-Bromo-5-fluoro-4-hydroxymethylphenyl)-methanol

5-Bromo-2-fluoro-4-hydroxymethyl-benzaldehyde (604.3 mg, 2.59 mmol) was dissolved in methanol (5 mL). To the resultant solution was added sodium borohydride (98.1 mg, 2.59 mmol) at 0° C. After stirring for 10 minutes, about 3 mL of methanol was removed by distillation. Water was added to the solution, and the resultant mixture was extracted with ethyl acetate. The organic layer was concentrated under reduced pressure. The resulting residue was purified by silica gel flash column chromatography (developing solution methanol:dichloromethane (3:100)), to thereby obtain the titled compound (247.3 mg, 43%).

1. customabout 3 mL of methanol was removed by distillation
2. additionWater was added to the solution
3. extractionthe resultant mixture was extracted with ethyl acetate
4. concentrationThe organic layer was concentrated under reduced pressure
5. customThe resulting residue was purified by silica gel flash column chromatography (developing solution methanol:dichloromethane (3:100))

ORD record

ord-fff64f7bdc824ee99d91b34bbc1c86e5

Source dataset

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08207134B2