Sodium Hydroxide → 2'-(Difluoromethyl)-2-methylbiphenyl-4-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

A 5 N aqueous solution of NaOH (1.5 mL, 7.5 mmol) was added into a solution of methyl 2′-(difluoromethyl)-2-methylbiphenyl-4-carboxylate (1.4 g, 5.1 mmol) in EtOH (15 mL). The resulting mixture was heated at 70° C. for 1 hour, and then evaporated. The residue was taken up with water (25 mL) and a 5N aqueous solution of HCl (3 mL), and then extracted with MTBE (2×50 mL). The organic layers were washed with brine (25 mL), combined, dried (MgSO4) and concentrated reduced pressure to give the title compound as a white powder (1.3 g, 93%). HPLC (Method A) Rt 4.2 min (purity: 98.9%). LC/MS (Method B): 261.1 (M−H)−. 1H NMR (DMSO-d6, 300 MHz) δ 13.1 (s, 1H), 7.90 (s, 1H), 7.82 (dd, J=7.9, 1.4 Hz, 1H), 7.74 (m, 1H), 7.66-7.55 (m, 2H), 7.26 (m, 2H), 6.55 (t, J=55 Hz, 1H), 2.05 (s, 3H).

Provenance & Evidence