Water → 2-(Acetylamino)-5-(1-methylethyl)benzoic acid

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Reaction Steps

A mixture of Example 2A (3.33 g, 13.0 mmol), and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex (1.00 g, 1.2 mmol) in triethylamine (5.5 mL), dimethylformamide (25 mL), and water (5 mL) was shaken at 120° C. in a reactor pressurized with 850 psi of CO for 18 hours. The mixture was filtered, the filter cake was washed with ethyl acetate, and the combined filtrates were partitioned between diethyl ether and 1M NaOH. The aqueous phase was acidified with 12M HCl and extracted twice with ethyl acetate. The combined extracts were washed with brine, dried (MgSO4), filtered, and concentrated to provide the desired product (2.38 g). MS (ESI(+)) m/e 222 (M+H)+, 244 (M+Na)+; (ESI(−)) m/e 220 (M−H)−.

Provenance & Evidence