Hydrochloric Acid → 2-(3,5-Dimethylphenyl)-4-nitrobenzoic acid

Participants

Reaction Conditions

Reaction Steps

2-bromo-4-nitrobenzoic acid (0.50 g, 2.03 mmol) and 3,5-dimethylphenyl boronic acid (0.34 g, 2.23 mmol) were dissolved into anhydrous DMF (dimethylformamide) (25 ml) under nitrogen. To this mixture was added Cs2CO3 (1.66 g, 5.08 mmol) followed by Pd(Ph3P)4 (0.12 g, 5%). The mixture was heated at 100° C. overnight. The solution was poured onto 1N HCl and extracted into Et2O. It was dried over MgSO4 and the solvent was removed in vacuo. The crude material was chromatographed on silica gel using a 9:1 mixture of hexanes and ethyl acetate to yield 0.34 g (61.7%) of pure product. 1H NMR (CDCl3) 2.36 (6 H, s), 6.99 (2 H, s), 7.07 (1 H, s), 8.03 (1 H, d, J=9.0 Hz), 8.23-8.25 (2 H, m); 13C NMR (CDCl3) 21.28, 121.68, 123.68, 125.74, 126.07, 130.22, 131.19, 131.31, 135.04, 138.21, 144.74, 170.75.

Provenance & Evidence