Sodium borohydride → HCID 68193211, compound

Ethyl (4′-bromobiphenyl-4-yl)(difluoro)acetate (2.8 g, 7.8 mmol) was dissolved in methanol (20 mL), and sodium borohydride (0.59 g, 16 mmol) was added at 0° C., followed by stirring at room temperature for 30 minutes. The reaction solution was concentrated under reduced pressure, and hydrochloric acid (1 M) was added to the residue, which was subsequently extracted with ethyl acetate, and the organic layer was dried over anhydrous sodium sulfate. After the solvent was distilled off under reduced pressure, the resulting residue was purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: hexane/ethyl acetate), and a fraction corresponding to the Rf value=0.50 (hexane/ethyl acetate=1/1) by thin layer chromatography was concentrated under reduced pressure to afford the title compound (2.4 g, 7.7 mmol) as a white solid (yield 99%).

1. concentrationThe reaction solution was concentrated under reduced pressure, and hydrochloric acid (1 M)
2. additionwas added to the residue, which
3. extractionwas subsequently extracted with ethyl acetate
4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
5. distillationAfter the solvent was distilled off under reduced pressure
6. customthe resulting residue was purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: hexane/ethyl acetate)
7. concentrationa fraction corresponding to the Rf value=0.50 (hexane/ethyl acetate=1/1) by thin layer chromatography was concentrated under reduced pressure

ORD record

ord-90dcde1c70574796a51e65f02652916e

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08785462B2