Trichloroacetyl chloride → 2-(Trichloroacetyl)pyrrole

HRID 992675Notes

Reaction equation

[NH:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.[Cl:6][C:7]([Cl:12])([Cl:11])[C:8](Cl)=[O:9]>>[Cl:6][C:7]([Cl:12])([Cl:11])[C:8]([C:2]1[NH:1][CH:5]=[CH:4][CH:3]=1)=[O:9]

Participants

Reactant 2

HCID 6420Trichloroacetyl chloride

HCID 8027Pyrrole

Product 1

HCID 3214872-(Trichloroacetyl)pyrroleYield 80%

Procedure

2-(Trichloroacetyl)pyrrole was prepared from pyrrole (12.5 g, 186 mmol) and trichloroacetyl chloride (36.5 g, 200 mmol) according to the method of Bailey et al, Org. Synth., 1971, 100. In this manner the title compound (31.3 g, 80%) was obtained as a cream solid, m.p. 73-74° C. (lit. m.p. 73-75° C.). 1H n.m.r. d 9.30, broad s, 1H; 7.39, m, 1H; 7.17, m, 1H; 6.40, dt, J 3.9 and 2.4 Hz, 1H. (see also J. Org. Chem., 1972, 37, 3618; 1993, 58, 7245).

Sources & evidence

ORD record: ord-8a03ca2ef23945ada5f958774b93c2ab
Source dataset: uspto-grants-2002_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06469171B1

Reaction notes

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