Water → HCID 18969606, compound

HRID 399026Notes

Reaction equation

HRID 399026 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10]([C:23]([F:26])([F:25])[F:24])=[CH:11][C:12]=2[S:13]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)(=[O:15])=[O:14])=[CH:4][CH:3]=1.[Br:27]Br.C([O-])(=O)C.[Na+].O>C(O)(=O)C.BrBr>[Br:27][C:11]1[C:12]([S:13]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)(=[O:14])=[O:15])=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[NH:9][C:10]=1[C:23]([F:25])([F:24])[F:26]

Participants

7

Reactant 4

HCID 962WaterHCID 24408BromineHCID 517045Sodium AcetateHCID 18969600HCID 18969600, compound

Product 1

HCID 18969606HCID 18969606, compoundYield 73.6%

Reagents, catalysts & solvents 2

HCID 24408BromineCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 2-(p-chlorophenyl)-3-[(p-chlorophenyl)sulfonyl]-5-(trifluoromethyl)pyrrole (2.15 g, 5.12 mmol), bromine (0.29 mL, 5.63 mmol) and sodium acetate (0.46 g, 5.63 mmol) in acetic acid is stirred at room temperature for 4 hours, treated with additional bromine (3 drops), stirred overnight at room temperature and poured into water. The resultant aqueous mixture is filtered to obtain a solid. Flash column chromatography of the solid using silica gel and a 1:5 ethyl acetate/hexanes solution gives the title product as a white solid (1.88 g, mp >230° C.).

Workup

  1. filtrationThe resultant aqueous mixture is filtered
  2. customto obtain a solid

Sources & evidence

ORD record
ord-0b819227184f42ea858a36c3beba7f10
Source dataset
uspto-grants-1998_10
Patent number
US05817691

Reaction notes

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