Chloroform → Methyl 4-amino-3,5-dichlorobenzoate

Participants

Reaction Steps

Methyl 4-aminobenzoate (25 g.) in dry chloroform (250 ml.) was treated dropwise with sulphuryl chloride (10 ml.) and the mixture heated at reflux for 4 hours. A further supply of sulphuryl chloride (10 ml.) was added and heating continued for a further 2 hours. The reaction mixture was poured onto ice and 2N sodium hydroxide solution was added. The organic solution was separated and the aqueous phase extracted with ethyl acetate. The combined organic solution was dried (anhydrous magnesium sulphate) and evaporated to give methyl 4-amino-3,5-dichlorobenzoate as a solid.

Provenance & Evidence