Br[C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C(=O)([O-])[O-].[K+].[K+].[NH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl>C(OCCO)C.O.[Cu].[Cu-]=O>[Cl:11][C:9]1[CH:8]=[CH:7][C:3]([C:4]([OH:6])=[O:5])=[C:2]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:10]=1
A solution of 2-bromo-4-chlorobenzoic acid (25.0 g, 106.0 mmol) in 2-ethoxy ethanol (40 mL) was treated with copper powder (0.74 g, 11.6 mmol), copper (I) oxide (0.76 g, 5.3 mmol) and potassium carbonate (15.8 g, 114.0 mmol) at 25° C. under nitrogen. The reaction was stirred at 25° C. for 5 min. At this time, the reaction was treated with aniline (11.2 mL, 124 mmol) and then was heated 135° C. for 48 h. At this time, the reaction was cooled to 25° C., diluted with water (30 mL) and was acidified with a 1N aqueous hydrochloric acid solution. The resulting mixture was stirred at 25° C. overnight. At this time, the resulting precipitate was collected by filtration through a sintered glass funnel. The solids were washed with an excess amount of water (2×100 mL) and then were dried under high vacuum to afford 4-chloro-2-phenylamino-benzoic acid (19 g, 72.3%) as a brown solid. This material was used without further purification.
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