[Br:1][C:2]1[C:3]2[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][C:4]=2[S:5][C:6]=1[C:7]([O:9]CC)=[O:8].[OH-].[K+]>CO.O>[Br:1][C:2]1[C:3]2[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][C:4]=2[S:5][C:6]=1[C:7]([OH:9])=[O:8]A solution of ethyl 3-bromo-4-methyl-benzo[b]thiophene-2-carboxylate (23b) (640 mg, 2.14 mmol) and potassium hydroxide (1.17 g, 21 mmol) in a mixture of methanol (10 mL) and water (5 mL) was warmed at 70° C. After 1 hour, methanol was evaporated and water (10 mL) was added to the reaction mixture which was washed with diethyl ether (10 mL). The aqueous layer was acidified to pH 2 with a hydrochloric acid solution 1N and extracted with ethyl acetate (2×10 mL). The organic layer was washed with brine (10 mL), dried over sodium sulfate, filtered and evaporated under reduced pressure to afford the desired acid (23c) as a white solid without further purification (420 mg, 1.55 mmol, 72%).
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