Allyl bromide → 2-(3,4-Dichlorophenyl)pent-4-enenitrile

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 3,4-dichlorophenylacetonitrile (800 g, 4.3 mol) in cyclohexane (16 l) at room temperature was carefully added aqueous sodium hydroxide solution (containing 1600 g of sodium hydroxide in 8 l of water). This addition caused an elevation of the reaction temperature to 50° C. Allyl bromide (572 g, 1.1 mol. equiv.) and tetra-n-butylammonium chloride hydrate (40 g, 0.03 mol. equiv.) were then added and the reaction stirred for one hour at 50° C. The aqueous phase was removed and the organic layer washed with water (10 l). The organic phase was filtered through silica gel (1 kg) under reduced pressure to give a yellow filtrate solution. The solvent was removed from the filtrate under reduced pressure to give the title compound as an oil (960 g) of 70% purity which was used without any further purification. TLC Rf=0.71 (silica, diethyl ether:hexane, 1:1, by volume). LRMS m/z=226 (m)+.

Provenance & Evidence