Chloroform → 1-(2-Bromoethenyl)-4-methoxynaphthalene

Participants

Reaction Steps

To a suspension of 33.3 g. (0.146 mol.) of 1-(2-carboxyethenyl)-4-methoxynaphthalene in 500 ml. of chloroform was added dropwise a solution of 8.05 ml. (0.146 mol.) of bromine in 125 ml. of methylene chloride. The solvent was removed, a solution of 31 g. (0.292 mol.) of sodium carbonate in 300 ml. of water was added to the residue and the mixture was refluxed for 2 hours. After cooling, the mixture was extracted with methylene chloride, the layers were separated and the organic phase was washed with water and saturated sodium chloride solution, dried (MgSO4) and evaporated to dryness to give 1-(2-bromoethenyl)-4-methoxynaphthalene.

Provenance & Evidence