Sodium Carbonate → 2-Chloro-5-(3-methylphenyl)benzoic acid

Participants

Reaction Conditions

Reaction Steps

2-Chloro-5-iodobenzoic acid (2.00 g, 7.08 mmol), m-tolylboronic acid (1.15 g, 8.50 mmol), Na2CO3 (2.70 g, 25.5 mmol) and Pd(OAc)2 (94 mg, 0.42 mmol) were dissolved in water (9 mL) and heated at 50° C. for 2 hours. The mixture was filtered and washed with water and filtrate was acidified with 2.5 M HCl, extracted into ethyl acetate and dried over anhydrous Na2SO4, the solvent was evaporated in vacuo to obtain crude 4-chloro-3′-methylbiphenyl-3-carboxylic acid as a grey solid in quantitative yield. 1H NMR (300 MHz, DMSO-d6): δ 8.03 (s, 1H), 7.83 (d, J=8.1 Hz, 1H), 7.63 (d, J=7.8 Hz, 1H), 7.55-7.50 (m, 2H), 7.40 (t, J=7.8 Hz, 1H), 7.25 (d, J=6.6 Hz, 1H), 2.41 (s, 3H).

Provenance & Evidence