4-Chloroaniline → HCID 86640285, compound

Participants

Reaction Steps

A solution of 2-azido-4,5-difluoro-benzoic acid (26.2 g, 132 mmol; Grieder A.; Thomas, A. W., Synthesis (2003), (11), 1707-1711) in thionyl chloride (216 ml) was stirred under reflux conditions for 1.5 h. The solvent was removed under reduced pressure to give the corresponding crude acid chloride which was suspended in dichloromethane (200 ml). 4-Chloroaniline (16.8 g, 132 mmol) was added and the mixture was stirred at ambient temperature for 14 h. Under ice cooling saturated NaHCO3 solution was added until pH 8 was reached. The mixture was extracted two times with dichloromethane, the combined extracts were washed with ice water/brine 1/1 and dried over Na2SO4. The solvent was removed under reduced pressure to give a brown solid which was crystallized from dichloromethane/n-heptane to give the title compound (18.5 g, 60 mmol; 46%) as yellow crystals.

Provenance & Evidence