Trichloroacetyl chloride → 2-(Trichloroacetyl)pyrrole

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).

1. custompurge
2. temperatureto reflux slightly during addition
3. temperatureRefluxing
4. customwas quenched slowly with a solution of Na2CO3 (65 g) in water (200 mL)
5. customThe layers were separated
6. washthe red organic layer was washed four times with water
7. dry with materialonce with brine and finally dried over Na2SO4
8. additionThe red ether solution was then treated twice with Norite (5 g)
9. filtrationfiltered through Celite
10. customThe solvent was removed under vacuum

ORD record

ord-0df952dc04254a7fbe51f18b82fa6b98

Source dataset

uspto-grants-2004_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06696575B2