3-(4-bromophenyl)-3-hydroxypropanenitrile

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A suspension of 4-bromobenzoylacetonitrile (500 mg) in ethanol (5 mL) and acetic acid (300 μL) was heated with sodium cyanoborohydride (280 mg) using an 80° C. hot plate for 2 hours. After cooling to ambient temperature, the mixture was diluted with water and concentrated to a syrup, which was diluted with ethyl acetate and washed with water, sat. NaHCO3, and brine. The extract was dried with mgSO4, filtered, and evaporated to provide 510 mg of a cloudy oil, which was filtered through silica gel using 1:1 ethyl acetate/hexane to provide the product (496 mg) as a thick oil. using an 80° C. for 2 hours concentrated to a syrup, which was diluted with ethyl acetate washed with water, sat. NaHCO3, and brine The extract was dried with mgSO4 filtered evaporated to provide 510 mg of a cloudy oil, which was filtered through silica gel using 1:1 ethyl acetate/hexane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A suspension of 4-bromobenzoylacetonitrile (500 mg) in ethanol (5 mL) and acetic acid (300 μL) was heated with sodium cyanoborohydride (280 mg) using an 80° C. hot plate for 2 hours. After cooling to ambient temperature, the mixture was diluted with water and concentrated to a syrup, which was diluted with ethyl acetate and washed with water, sat. NaHCO3, and brine. The extract was dried with MgSO4, filtered, and evaporated to provide 510 mg of a cloudy oil, which was filtered through silica gel using 1:1 ethyl acetate/hexane to provide the product (496 mg) as a thick oil. using an 80° C. for 2 hours concentrated to a syrup, which was diluted with ethyl acetate washed with water, sat. NaHCO3, and brine The extract was dried with MgSO4 filtered evaporated to provide 510 mg of a cloudy oil, which was filtered through silica gel using 1:1 ethyl acetate/hexane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A suspension of 4-bromobenzoylacetonitrile (500 mg) in ethanol (5 mL) and acetic acid (300 μL) was heated with sodium cyanoborohydride (280 mg) using an 80° C. hot plate for 2 hours. After cooling to ambient temperature, the mixture was diluted with water and concentrated to a syrup, which was diluted with ethyl acetate and washed with water, sat. NaHCO3, and brine. The extract was dried with mgSO4, filtered, and evaporated to provide 510 mg of a cloudy oil, which was filtered through silica gel using 1:1 ethyl acetate/hexane to provide the product (496 mg) as a thick oil. using an 80° C. for 2 hours concentrated to a syrup, which was diluted with ethyl acetate washed with water, sat. NaHCO3, and brine The extract was dried with mgSO4 filtered evaporated to provide 510 mg of a cloudy oil, which was filtered through silica gel using 1:1 ethyl acetate/hexane