3-Methylbenzoic acid → 2-(3,5-Bis(trifluoromethyl)phenyl)-5-Methylbenzoic Acid

Participants

Reaction Steps

Palladium acetate (11.4 mg, 0.05 mmol), AgOAc (217 mg, 1.3 mmol), 3-methylbenzoic acid (136 mg, 1.0 mmol, 3,5-bis(trifluoromethyl)iodobenzene (1.02 g, 3.0 mmol and acetic acid (200 μL) were combined and heated at 120° C. for 4.5 h. After purification white solid was obtained, 207 mg (59%), mp 217-219° C. (isooctane). Rf-0.60 (1/9 ethyl acetate-dichloromethane). 1H NMR (300 MHz, acetone-d6): δ 2.46 (s, 3H), 7.38-7.51 (m, 2H), 7.87 (s, 1H), 7.94 (s, 2H), 8.00 (s, 1H), 11.3 (brs, 1H). 13C NMR (75 MHz, acetone-d6) 320.6, 120.9 (br s), 124.2 (q, J-271.1 Hz), 129.7 (br s), 130.8, 131.1 (q, J-33.3 Hz), 131.5, 131.7, 133.1, 137.6, 139.3, 144.9, 168.0. FT-IR (neat, cm1) υ 1689, 1290, 1121. Anal. calcd for C16H10F6O2 (348.2 g/mol) C, 55.18; H, 2.89. Found: C) 55.07; H, 2.81. The 1H NMR and 13C NMR spectra are shown in FIGS. 24A&B, respectively.

Provenance & Evidence