Sodium borohydride → 1-(3-bromophenyl)-3-hydroxyCyclobutanecarbonitrile

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Reaction Steps

1-(3-Bromophenyl)-3-oxocyclobutanecarbonitrile (2.00 g, 8.00 mmol) was dissolved in DCM (15 mL) and MeOH (15.00 mL), and the mixture was cooled to 0° C. Sodium borohydride (0.333 g, 8.80 mmol) was added to the reaction mixture, and stirring was continued at 0° C. for 1.5 hours. The reaction mixture was quenched with water at 0° C. then warmed to RT. DCM was added, and the mixture was washed with water and brine. The organic layer was dried over sodium sulfate and concentrated under vacuum to afford 2.02 g of 1-(3-bromophenyl)-3-hydroxycyclobutanecarbonitrile (2.02 g, 8.01 mmol, 100% yield) as a pale yellow oil. Mass cal'd: 250.99; MS (ESI pos. ion) m/z: 252.0 [M+H].

Provenance & Evidence