Trichloroacetyl chloride → 2-(Trichloroacetyl)pyrrole

Participants

Reaction Steps

Under a nitrogen atmosphere to a solution of trichloroacetyl chloride (45 g, 246 mmol) in ether was added dropwise a solution of pyrrole (15.6 g, 233 mmol) in ether over 3 hours. The heat of reaction caused the mixture to reflux during the addition. Following the addition the mixture was stirred for 1 hour. Under cooling (5° C.) a solution of potassium carbonate (20 g, 145 mmol) in water was added slowly. The layers were separated and the organic phase was washed with brine, dried (MgSO4), filtered, treated with charcoal and filtered. The solvent was removed in vacuo and the residue was dissolved in hexane. The dark colored solution was cooled in the refrigerator and the product crystallized (38 g, 77% yield, tan solid), 1H NMR (400 MHZ, DMSOd6) δ 6.31-6.33 (m, 1H), 7.27-7.31 (m, 2H), MS m/e (M−H)− 209.9.

Provenance & Evidence