Sodium Hydroxide → 4-Bromo-3-cyano-5-ethyl-1H-pyrrole-2-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

N-Bromosuccinimide (289 mg, 1.63 mmol) was added to a cooled solution of 3-cyano-5-ethyl-1H-pyrrole-2-carboxylic acid methyl ester (Intermediate 27; 290 mg, 1.63 mmol) in anhydrous DCM at 0° C. The mixture was stirred at 0° C. for 30 minutes. The mixture was poured into a cold solution of 2 N sodium hydroxide (15 ml) and extracted with DCM. The combined extracts were washed with water (2×15 ml), dried over sodium sulphate and concentrated in vacuo to give small amounts of title compound. The aqueous phase was acidified, extracted with EtOAc, concentrated in vacuo to give the title compound as a creamy brown solid (240 mg).

Provenance & Evidence