Sodium borohydride → 1-(5-Bromo-2-fluorophenyl)-2,2-difluoropropane-1,3-diol

To a solution of ethyl 3-(5-bromo-2-fluorophenyl)-2,2-difluoro-3-hydroxypropanoate (20.0 g, 61.3 mmol) in MeOH (160 mL), NaBH4 (7.0 g, 184.2 mmol) was added portion wise over a period of 30 min. at 0° C. Stirring was continued for 1 h at 0° C. and reaction was monitored by TLC. Upon complete consumption of the starting material, reaction mass was concentrated under reduced pressure and treated with saturated ammonium chloride solution. The crude reaction mass was dissolved in ethyl acetate and organic layer was washed with brine (15 mL) followed by drying over anhydrous Na2SO4. The organic layer was concentrated under reduced pressure to furnish title compound with sufficient purity. Yield=17 g (97%). TLC (50% ethyl acetate in Hexane): Rf=0.32),

1. customreaction
2. customUpon complete consumption of the starting material, reaction mass
3. concentrationwas concentrated under reduced pressure
4. additiontreated with saturated ammonium chloride solution
5. customThe crude reaction mass
6. washorganic layer was washed with brine (15 mL)
7. dry with materialby drying over anhydrous Na2SO4
8. concentrationThe organic layer was concentrated under reduced pressure

ORD record

ord-dc6b0facbdf14e0fb55e0b032730cbed

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08846658B2