(5-Bromopyridin-2-yl)acetic acid → 2-(5-Bromopyridin-2-yl)ethan-1-ol

Commercially available 2-(5-bromopyridin-2-yl)acetic acid (1.00 g, 4.6 mmol) in tetrahydrofuran (10 mL) is cooled to 5° C. and treated dropwise over 10 minutes with borane-tetrahydrofuran complex (13.9 mL, 13.9 mmol). After stirring at room temperature for 4 hours, the reaction mixture is quenched with saturated aqueous potassium carbonate (20 mL), extracted with ethyl acetate (50 mL), dried over MgSO4, filtered, the solvent removed under reduced pressure, and the crude material purified by column chromatography on silica gel eluting with a gradient of neat heptane to neat ethyl acetate to afford the title compound (1.09 g): m/z (Cl) 203 [M+H].

1. additiontreated dropwise over 10 minutes with borane-tetrahydrofuran complex (13.9 mL, 13.9 mmol)
2. customthe reaction mixture is quenched with saturated aqueous potassium carbonate (20 mL)
3. extractionextracted with ethyl acetate (50 mL)
4. dry with materialdried over MgSO4
5. filtrationfiltered
6. customthe solvent removed under reduced pressure
7. customthe crude material purified by column chromatography on silica gel eluting with a gradient of neat heptane to neat ethyl acetate

ORD record

ord-303d9ac953ec493da25569dda8632d2f

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09206126B2