Hydrochloric Acid → 4-Nitro-3-(trifluoromethyl)benzenesulfonyl chloride

Participants

Reaction Steps

A mixture containing 57.5 g (0.28 mole) of 4-nitro-2-(trifluoromethyl)aniline in 200 ml of concentrated hydrochloric acid was heated to 90° for 15 minutes and left stirring at ambient temperature for 18 hours. The resulting mixture was chilled to 4° and diazotized with 21.4 g (0.31 mole) of sodium nitrite in 50 ml of water. After one hour, the diazonium salt solution was added dropwise over 20 minutes and with stirring to a cold (5°-10°) solution containing 13 g of cupric chloride and 64 g of sulfur dioxide in 250 ml of glacial acetic acid. After two hours, the mixture was filtered. The filter cake was washed well with water and dried to give 68 g (84%) of product as a light tan solid; m.p. 77°-79° C.

Provenance & Evidence