N[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]([F:14])([F:13])[F:12])[C:5]([OH:7])=[O:6].[I:15]C(I)I.N(OCCCC)=O>C1COCC1>[I:15][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]([F:14])([F:13])[F:12])[C:5]([OH:7])=[O:6]3-Amino-4-(trifluoromethyl)benzoic acid (commercially available) (6.5 g, 31.7 mmol) and triiodomethane (37.4 g, 95.1 mmol) were dissolved in THF (300 ml). The reaction mixture was heated to 80° C. and then butyl nitrite (5.56 ml, 47.6 mmol) was added slowly at this temperature. Heating was continued at this temperature for 4 hours and then the reaction was concentrated in vacuo to give the crude product. Purification by column chromatography (hexane to 30% EtOAc in hexane). This material was combined with another batch from a similar reaction performed on 2 g of 3-amino-4-(trifluoromethyl)benzoic acid. The combined material was purified by preparative HPLC to give the title compound (6.1 g). MS C8H4F3IO2 requires 316; found 315 (M−H+).
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