[CH3:1][C:2]1[C:3]([C:7]2[CH:16]=[CH:15][C:10]([C:11]([O:13]C)=[O:12])=[CH:9][C:8]=2[C:17]([F:20])([F:19])[F:18])=[CH:4][S:5][CH:6]=1.[OH-].[Na+]>CCO.O>[CH3:1][C:2]1[C:3]([C:7]2[CH:16]=[CH:15][C:10]([C:11]([OH:13])=[O:12])=[CH:9][C:8]=2[C:17]([F:20])([F:18])[F:19])=[CH:4][S:5][CH:6]=1A solution of methyl 4-(4-methyl-3-thienyl)-3-(trifluoromethyl)benzoate (3 g; 9.99 mmol; 1 eq.) in EtOH (90 mL) at RT was treated with sodium hydroxide (5.99 mL; 5 M; 29.97 mmol; 3 eq.). The reaction mixture was stirred at 60° C. for 2 hours. The reaction mixture was concentrated to give a brown solid which was taken up in water (300 mL) and the aqueous phase was washed twice with EtOAc. The aqueous phase was acidified with HCl cc to pH 2 and extracted with EtOAc (250 mL). The organic layer was dried over MgSO4 and concentrated affording the title compound as a brown oil (2.60 g, 90%). 1H NMR (DMSO-d6, 300 MHz) δ 13.07 (br s, 1H), 8.34-8.24 (m, 2H), 7.57-7.54 (m, 1H), 7.47-7.46 (m, 1H), 7.34-7.33 (m, 1H), 1.98 (s, 3H). LC/MS (Method A): 284.9 (M−H)−. HPLC (Method A) Rt 4.53 min (Purity: 95.5%).
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