Bromine → 3-Bromo-2-(p-chlorophenyl)-5-[(trifluoromethyl)thio]pyrrole

HRID 375184Notes

Reaction equation

HRID 375184 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10]([S:13][C:14]([F:17])([F:16])[F:15])=[CH:11][CH:12]=2)=[CH:4][CH:3]=1.[Br:18]Br>C(Cl)(Cl)Cl>[Br:18][C:12]1[CH:11]=[C:10]([S:13][C:14]([F:15])([F:17])[F:16])[NH:9][C:8]=1[C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 189304232-(p-Chlorophenyl)-5-[(trifluoromethyl)thio]pyrrole

Product 1

HCID 189304073-Bromo-2-(p-chlorophenyl)-5-[(trifluoromethyl)thio]pyrroleYield 80.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 2-(p-chlorophenyl)-5-[(trifluoromethyl)thio]pyrrole (1.94 g, 0.00699 mol) in chloroform is cooled, treated with a solution of bromine (1.16 g, 0.00699 mol) in chloroform, stirred for two hours, washed with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain a dark syrup. Flash chromatography of the syrup using silica gel and a 1:10 ethyl acetate/hexanes solution gives the title product as a pink syrup (2.0 g) which is identified by 1HNMR and 13CNMR spectral analyses.

Workup

  1. washwashed with water and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customto obtain a dark syrup

Sources & evidence

ORD record
ord-aa2cc8f95ccc4d029408157ec7f2d0ad
Source dataset
uspto-grants-1996_01
Patent number
US05484807

Reaction notes

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