2,4-Dichlorobenzoic Acid → BENZOIC ACID, 2-[(3-BROMOPHENYL)AMINO]-4-CHLORO-

Participants

Reaction Conditions

Reaction Steps

(Method D-2) Under an atmosphere of nitrogen, 2,4-dichlorobenzoic acid (36 g, 0.19 mol), 3-bromoaniline (48 g, 0.28 mol), potassium carbonate (32 g, 0.23 mol), and copper powder (1 g, 0.016 mol, catalytic) were mixed in dry DMF (150 ml) and heated to 150° C. for 18 hrs. The DMF was removed under reduced pressure, water (200 mL) added and the mixture acidified with 2M HCl (400 mL) to give a brown solid which was collected by filtration. Recrystallisation from ethanol/water (60/40) gave the title compound (43 g, 0.116 mol 61%) as a grey solid. See, for example, Hodgeman et al., 1972.

Provenance & Evidence