Chlorobenzene → 3-Chloro-4-(4-chlorophenyl)benzenamine

Participants

Reaction Conditions

Reaction Steps

2,4'-dichloro-4-nitro-biphenyl was prepared by dissolving 2-chloro-4-nitroaniline (2.6 g, 15 mmol) in chlorobenzene (20 mL, 200 mmol), heated to 120° C. under a nitrogen atmosphere. i-Amylnitrite (3.4 mL, 25 mmol) was added to the solution slowly over 1 h via a syringe pump and canula. After stirring for 12 h the reaction mixture was cooled to ambient temperature and the excess chlorobenzene was removed in vacuo. The residue after evaporation was chromatographed by filtration through silica gel as in Example 1A, using mixture of hexane and ethyl acetate (80:20) as the eluent. Further purification was achieved by chromatography [Chromatotron®, 4 mm silica gel, hexanes/methylene chloride, 80:20, 20 mL/min] which yielded the title compound (1.75 g). Mass spectrum: m/z at 267 for C12H7Cl2NO2.

Provenance & Evidence