Dichloromethane → (1,1'-Biphenyl)-2-carboxylic acid, 4'-methyl-, methyl ester

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Reaction Steps

A mixture of methyl 4-aminomethylbenzoate (0.50 g) (obtained by acid-catalysed esterification of 4-aminomethylbenzoic acid), 2,5 difluoronitrobenzene (0.40 g) and potassium carbonate (0.35 g) in DMF (5 ml) was heated at 100° for 5 hours. The mixture was cooled, dichloromethane (20 ml) was added and insoluble material was removed by filtration. The solvent was evaporated and the residue recrystallised from methanol/ethyl acetate to give methyl 4-N-(4-fluoro-2-nitrophenyl)aminomethylbenzoate (B) (0.54 g) as orange needles, m.p. 144°-146° C.; NMR (CDCl3): 3.92(s, 3H), 4.61(d, 2H), 6.70(dd, 1H), 7.17(ddd, 1H), 7.62(d, 2H), 7.93(dd, 1H), 8.04(d, 2H), 8.36(br s, 1H); microanalysis found: C, 59.0; H, 4.1; N, 9.0; C15H13FN2O4 requires: C, 59.2; H, 4.3; N, 9.2%.

Provenance & Evidence