Hydrogen Bromide → 2-Bromo-1-oxoindan-5-carbonitrile

Participants

Reaction Steps

3.93 g of 1-oxoindane-5-carbonitrile are dissolved in 40 ml of glacial acetic acid and, after addition of 0.1 ml of hydrobromic acid (48% strength in water), at room temperature a solution of 1.34 ml of bromine in 8 ml of acetic acid is added dropwise. The reaction mixture is stirred at room temperature for 3 h and then added to a mixture of 20 g of ice and 40 g of water, 0.5 g of sodium bisulfite is added and the mixture is extracted by shaking twice with 50 ml of dichloromethane each time. The organic phase is washed with 50 ml of water, dried over magnesium sulfate, concentrated in vacuo and chromatographed on silica gel with toluene/ethyl acetate 25/1. 2-Bromo-l-oxoindane-5-carbonitrile is obtained with a melting point of 115-118° C.

Provenance & Evidence