Trichloroacetyl chloride → 2-(Trichloroacetyl)pyrrole

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).

1. temperatureto reflux during addition
2. temperatureRefluxing
3. customThe layers were separated
4. washthe red organic layer was washed four times with water (4×50 mL)
5. dry with materialonce with brine (1×50 mL) and finally dried over anhydrous sodium sulphate
6. filtrationThe red ether solution was then filtered through CELITE®
7. washwashed with ether
8. customThe solvent was removed under vacuum

ORD record

ord-e807f0ee5eb24b17ac1ff00a65f02735

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08580959B2