Sodium borohydride → HCID 89701791, compound

3′-Fluoro-4′-hydroxy-2′,6′-dimethylbiphenyl-3-carbaldehyde 19a (700 mg, 2.87 mmol, prepared by a method disclosed in PCT patent application WO2008001931) was dissolved in 10 mL of methanol, followed by addition of sodium borohydride (130 mg, 3.44 mmol). The reaction solution was stirred for 2 hours. The resulting solution was concentrated under reduced pressure. The residue was mixed with 10 mL of water and extracted with ethyl acetate (50 mL×2). The combined organic extracts were washed with saturated sodium chloride solution (30 mL), dried with anhydrous magnesium sulphate, and filtered. The filtrate was concentrated under reduced pressure to obtain the crude title compound 3-fluoro-3′-(hydroxymethyl)-2,6-dimethylbiphenyl-4-ol 19b (700 mg) as a white solid, which was used directly in the next step without further purification.

1. concentrationThe resulting solution was concentrated under reduced pressure
2. additionThe residue was mixed with 10 mL of water
3. extractionextracted with ethyl acetate (50 mL×2)
4. washThe combined organic extracts were washed with saturated sodium chloride solution (30 mL)
5. dry with materialdried with anhydrous magnesium sulphate
6. filtrationfiltered
7. concentrationThe filtrate was concentrated under reduced pressure

ORD record

ord-ef2a9317ae334c06b27fd4b950c004e5

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09139548B2