Water → Benzonitrile, 2-(4-bromophenoxy)-5-nitro-

Participants

Reaction Conditions

Reaction Steps

To a solution of 5.31 g (0.0307 moles) of 4-bromophenol dissolved in 150 ml of DMSO was added 1.23 g (0.0307 moles) of NaOH. The slurry was heated at 60° C. for 15 minutes and 5.04 g (0.0276 moles) of 2-chloro-5-nitrobenzonitrile was added. The mixture was heated at 75° C. for 4 hrs. The reaction mixture was cooled and poured into water. The product was collected by filtration, washed well with water and dried, which gave 8.1 g of crude product. The crude product was dissolved in CH2Cl2 and washed with 10% aqueous NaOH, water and dried (Na2SO4). Removal of solvent in vacuo gave 7.5 g (85% yield) of product. Recrystallization from ethanol afforded purified 2-(4-bromophenoxy)-5-nitrobenzonitrile, mp 171°-172° C.

Provenance & Evidence