Bromine → 4-Bromo-2-(4-chlorophenyl)-1-methyl-5-(trifluoromethyl)pyrrole-3-carbonitrile

HRID 1885371Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH3:19])[C:10]([C:15]([F:18])([F:17])[F:16])=[CH:11][C:12]=2[C:13]#[N:14])=[CH:4][CH:3]=1.[Br:20]Br>ClC1C=CC=CC=1.C(OCC)(=O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]([CH3:19])[C:10]([C:15]([F:18])([F:16])[F:17])=[C:11]([Br:20])[C:12]=2[C:13]#[N:14])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 2-(p-chlorophenyl)-1-methyl-5-(trifluoromethyl)pyrrole-3-carbonitrile (5.70 g, 0.02 mol) in chlorobenzene is treated with bromine (3.52 g, 0.022 mol), heated at 80° C. for 20 hours, cooled to room temperature, treated with additional bromine (3.52 g, 0.022 mol) and heated at 100° C. until reaction is complete by HPLC analysis. The reaction mixture is cooled to room temperature and diluted with ethyl acetate and water. The organic phase is washed with aqueous sodium metabisulfite, dried (MgSO4) and concentrated in vacuo to afford a solid residue. The residue is recrystallized from ethyl acetate/heptane to give the title product as a white solid, 6.50 g (89.4% yield), mp 126°-129° C.

Workup

temperaturecooled to room temperature
temperatureheated at 100° C. until reaction
temperatureThe reaction mixture is cooled to room temperature
washThe organic phase is washed with aqueous sodium metabisulfite
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo
customto afford a solid residue
customThe residue is recrystallized from ethyl acetate/heptane

Sources & evidence

ORD record: ord-eecfa46de4a149aabb45ebe0dcb1230c
Source dataset: uspto-grants-1992_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05144041

Reaction notes

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