Trichloroacetyl chloride → 2-(Trichloroacetyl)pyrrole

Participants

Reaction Steps

To a mixture of anhydrous ether (130 mL) and trichloroacetyl chloride (95 mL; 0.85 mol) under a nitrogen purge was added pyrrole (50.03 g, 0.75 mol) dissolved in anhydrous ether (400 mL) via a dropping funnel over a 2-hour period. The now violet ether solution began to reflux slightly during addition. Refluxing was continued for an additional 1 hour before the reaction was quenched slowly with a solution of Na2CO3 (65 g) in water (200 mL). The layers were separated, and the red organic layer was washed four times with water and once with brine and finally dried over Na2SO4. The red ether solution was then treated twice with Norite (5 g) and filtered through Celite. The solvent was removed under vacuum to give the title compound (134.7 g, 0.63 mol, 85%). 1H-NMR (CDCl3): δ 9.65 (br s, 1H), 7.40 (m, 1H), 7.18 (m, 1H), 6.39 (dd, 1H).

Provenance & Evidence