Trichloroacetyl chloride → 2-(Trichloroacetyl)pyrrole

Participants

Reaction Steps

To trichloroacetyl chloride (48 mL; 0.43 mol) taken in anhydrous ether (150 mL) under nitrogen was added pyrrole (25 g, 0.37 mol) dissolved in anhydrous ether (500 mL) through a dropping funnel over a 2-hour period. The violet ether solution began to reflux during addition. Refluxing was continued for 1 h before the reaction was quenched with a solution of sodium carbonate (33 g, 0.31 mol) in water (200 mL). The layers were separated and the red organic layer was washed four times with water (4×50 mL) and once with brine (1×50 mL) and finally dried over anhydrous sodium sulphate. The red ether solution was then filtered through CELITE® and washed with ether. The solvent was removed under vacuum to afford 2-trichloroacetylpyrrole (Example 1A, 72 g, 91% yield).) as an ash colored solid (72 g, 91% yield). LC-MS, [M−H]+=212. 1H NMR (DMSO-d6, 300 MHz): δ 9.63 (brs, 1H), 7.39 (m, 1H), 7.19 (m, 1H), 6.40 (m, 1H).

Provenance & Evidence