Water → 3-Bromo-5-(p-chlorophenyl)-4-nitro-2-[(trifluoromethyl)thio]pyrrole

HRID 1975201Notes

Reaction equation

HRID 1975201 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10]([S:16][C:17]([F:20])([F:19])[F:18])=[CH:11][C:12]=2[N+:13]([O-:15])=[O:14])=[CH:4][CH:3]=1.C([O-])(=O)C.[Na+].[Br:26]Br.O>C(O)(=O)C>[Br:26][C:11]1[C:12]([N+:13]([O-:15])=[O:14])=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[NH:9][C:10]=1[S:16][C:17]([F:18])([F:20])[F:19]

Participants

6

Reactant 4

HCID 962WaterHCID 24408BromineHCID 517045Sodium AcetateHCID 189303872-(p-Chlorophenyl)-3-nitro-5[(trifluoromethyl)thio]pyrrole

Product 1

HCID 189304473-Bromo-5-(p-chlorophenyl)-4-nitro-2-[(trifluoromethyl)thio]pyrroleYield 56.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of 2-(p-chlorophenyl)-3-nitro-5[(trifluoromethyl)thio]pyrrole (0.35 g, 0.0011 mol) and sodium acetate (0.11 g, 0.0013 mol) in acetic acid is treated with a solution of bromine (0.21 g, 0.0013 mol) in acetic acid, stirred for one hour, poured into water and extracted with ethyl acetate. The combined organic extracts are washed with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain a residue. Flash chromatography of the residue using silica gel and a 1:9 ethyl acetate/hexanes solution gives the title product as a yellow solid (0.25 g, mp 160°-165° C.) which is identified by 1HNMR, 19FNMR and 13CNMR spectral analyses.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic extracts are washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customto obtain a residue

Sources & evidence

ORD record
ord-1b48a1964aad4924846c8b2dee9d6e36
Source dataset
uspto-grants-1994_02
Patent number
US05284863

Reaction notes

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