Bromine → 4-Chloro-2-(4-chlorophenyl)-5-trifluoromethyl)-1H-pyrrole-3-carbonitrile

HRID 2399544Notes

Reaction equation

HRID 2399544 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10]([C:15]([F:18])([F:17])[F:16])=[CH:11][C:12]=2[C:13]#[N:14])=[CH:4][CH:3]=1.C([O-])(=O)C.[Na+].BrBr.S(Cl)([Cl:29])(=O)=O>C(O)(=O)C>[Cl:29][C:11]1[C:12]([C:13]#[N:14])=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[NH:9][C:10]=1[C:15]([F:18])([F:16])[F:17]

Participants

6

Reactant 4

HCID 24408BromineHCID 24648Sulfuryl chlorideHCID 517045Sodium AcetateHCID 110001432-(4-chlorophenyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile

Product 1

HCID 1787184-Chloro-2-(4-chlorophenyl)-5-trifluoromethyl)-1H-pyrrole-3-carbonitrileYield 84%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 2-(p-chloropheny1)-5-(trifluoromethyl)pyrrole-3-carbonitile (8.12 g, 0.03 mol) and sodium acetate (0.25 g, 0.003 mol) in acetic acid at 70° C. is treated dropwise with bromine (0.48 g, 0.003 mol). When the color has disappeared, the reaction mixture is treated dropwise with sulfuryl chloride (6.1 g, 0.045 mol) over a 1 hour period, held at 70° C. for 1 hour, concentrated in vacuo and diluted with water. The reaction mixture is filtered, the filter cake is washed with water and dried to yield the title product as a white solid, 7.7 g (84% yield), mp 242°-243° C.

Workup

  1. concentrationconcentrated in vacuo
  2. additiondiluted with water
  3. filtrationThe reaction mixture is filtered
  4. washthe filter cake is washed with water
  5. customdried

Sources & evidence

ORD record
ord-228cc80bc8ba410d9cda243787e60908
Source dataset
uspto-grants-1995_09
Patent number
US05449789

Reaction notes

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