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

HRID 2399545Notes

Reaction equation

HRID 2399545 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>C(Cl)(Cl)(Cl)Cl>[Br:20][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)[N:9]([CH3:19])[C:10]=1[C:15]([F:18])([F:16])[F:17]

Participants

4

Reactant 2

HCID 24408BromineHCID 118221892-(4-chlorophenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile

Product 1

HCID 1835584-Bromo-2-(4-chlorophenyl)-1-methyl-5-(trifluoromethyl)pyrrole-3-carbonitrileYield 94%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 2-(p-chlorophenyl)-1-methyl-5-(trifluoromethyl)pyrrole-3-carbonitrile (5.0 g, 0.0176 mol) in carbon tetrachloride is treated with bromine (56 g, 0.0351 mol), heated at reflux temperature for 8 hours, cooled, washed sequentially with water, aqueous sodium metabisulfite and water, dried over sodium sulfate and concentrated in vacuo to give a solid residue. The residue is recrystallized from heptane to give the title product as a white solid, 6.0 g (94% yield), mp 126°-129° C.

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for 8 hours
  3. temperaturecooled
  4. washwashed sequentially with water, aqueous sodium metabisulfite and water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customto give a solid residue
  8. customThe residue is recrystallized from heptane

Sources & evidence

ORD record
ord-594dc18f52084b7fb8da74b7e0f8e1e9
Source dataset
uspto-grants-1995_09
Patent number
US05449789

Reaction notes

Loading…