Bromoacetonitrile → Tert-butyl 3-(3-chlorophenyl)-3-(cyanomethoxy)propyl(methyl)carbamate

Participants

Reaction Steps

To a suspension of NaH (0.65 g, 27 mmol) and tert-butyl 3-(3-chlorophenyl)-3-hydroxypropyl(methyl)carbamate (2.7 g, 9 mmol) in CH3CN (60 mL) at 0-5° C. was added drop wise a solution of bromoacetonitrile (3.3 g, 27 mmol) in CH3CN (20 mL), the reaction mixture was stirred for overnight at room temperature. The reaction mixture was poured into saturated aqueous NH4Cl, ethyl acetate (50 mL) was added. The organic layer was washed with water (3×20 mL) and brine, dried over Na2SO4, filtered and concentrated in vacuo to afford the crude product, which was used for the next step without purification.

Provenance & Evidence