Trichloroacetyl chloride → 2-(Trichloroacetyl)pyrrole

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.

1. temperatureThe heat of reaction
2. temperatureto reflux during the addition
3. additionthe addition the mixture
4. additionwas added slowly
5. customThe layers were separated
6. washthe organic phase was washed with brine
7. dry with materialdried (MgSO4)
8. filtrationfiltered
9. additiontreated with charcoal
10. filtrationfiltered
11. customThe solvent was removed in vacuo
12. dissolutionthe residue was dissolved in hexane
13. temperatureThe dark colored solution was cooled in the refrigerator
14. customthe 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

ORD record

ord-c15d9f914eec42209b2a4a0e0fe83efc

Source dataset

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07705030B2