Water → 2,3-Dibromo-1-(chloromethyl)-5-(p-chlorophenyl)-4-[(trifluoromethyl)sulfonyl]pyrrole

HRID 1975196Notes

Reaction equation

HRID 1975196 reaction equation
[Br:1][C:2]1[N:3]([CH2:22]NC(=O)C)[C:4]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)=[C:5]([S:8]([C:11]([F:14])([F:13])[F:12])(=[O:10])=[O:9])[C:6]=1[Br:7].O(Cl)[Cl:28].O>C(Cl)Cl>[Br:1][C:2]1[N:3]([CH2:22][Cl:28])[C:4]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)=[C:5]([S:8]([C:11]([F:14])([F:12])[F:13])(=[O:10])=[O:9])[C:6]=1[Br:7]

Participants

5

Reactant 3

HCID 962WaterHCID 24646Chlorine monoxideHCID 15278421N-{{2,3-Dibromo-5-(p-chlorophenyl)-4-[(trifluoromethyl)sulfonyl]pyrrol-1-yl}methyl}acetamide

Product 1

HCID 152784222,3-Dibromo-1-(chloromethyl)-5-(p-chlorophenyl)-4-[(trifluoromethyl)sulfonyl]pyrrole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-{{2,3-Dibromo-5-(p-chlorophenyl)-4-[(trifluoromethyl)sulfonyl]pyrrol-1-yl}methyl}acetamide (4.5 g, 0.00835 mol) is added to phosphoros oxychloride (15 mL). The reaction mixture is refluxed for 31/2 hours, poured into water, stirred overnight and filtered to obtain a solid. The solid is dissolved into methylene chloride and the solution is dried over anhydrous sodium sulfate and concentrated in vacuo to obtain the title product as a yellow solid (3.8 g, mp 153°-156° C.) which is identified by 1HNMR and 13CNMR spectral analyses.

Workup

  1. temperatureThe reaction mixture is refluxed for 31/2 hours
  2. filtrationfiltered
  3. customto obtain a solid
  4. dry with materialthe solution is dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-38ee375f47214b158f57d03190512379
Source dataset
uspto-grants-1994_02
Patent number
US05284863

Reaction notes

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