Sodium Hydroxide → 2-(4'-Cyanobiphenyl-2-ylthio)-2-methylpropanoic acid

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Reaction Conditions

Reaction Steps

A mixture of ethyl 2-(4′-cyanobiphenyl-2-ylthio)-2-methylpropanoate (93 mg, 0.286 mmol) and aqueous sodium hydroxide solution (1 M, 2 mL) in methanol (4 mL) was stirred at 60° C. for 12 hours. The reaction mixture was concentrated to remove methanol, acidified and filtered to obtain a white powder, which was purified by chromatography to yield 2-(4′-cyanobiphenyl-2-ylthio)-2-methylpropanoic acid (38.1 mg, 45%). By-product 2-(4′-carbamoylbiphenyl)-2-ylthio)-2-methylpropanoic acid (38.4 g) was also obtained. 1H NMR (400 MHz, DMSO-d6, 25° C.) 7.67-7.72 (m, 3H), 7.48-7.54 (m, 3H), 7.37-7.43 (m, 2H), 1.33 (s, 6H). MS (m/z) 296.16 (M-1).

Provenance & Evidence