Acetic Acid → HCID 19103167, compound

HRID 466628Notes

Reaction equation

HRID 466628 reaction equation
[Br:1]Br.[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[NH:12][C:11]=2[C:19]([F:22])([F:21])[F:20])=[CH:6][CH:5]=1.C(O)(=O)C.C([O-])(=O)C.[Na+]>O>[Br:1][C:14]1[C:10]([C:7]2[CH:6]=[CH:5][C:4]([Cl:3])=[CH:9][CH:8]=2)=[C:11]([C:19]([F:22])([F:20])[F:21])[NH:12][C:13]=1[C:15]([F:16])([F:17])[F:18]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 24408BromineHCID 517045Sodium AcetateHCID 19103164HCID 19103164, compound

Product 1

HCID 19103167HCID 19103167, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Bromine (0.527 g, 0.17 mL, 0.0033 mol) is added to a solution of 3-(p-chlorophenyl)-2,5-bis(trifluoromethyl)pyrrole (0.94 g, 0.003 mol), acetic acid (6 mL) and sodium acetate (0.984 g, 0.012 mol). After 1 hour the reaction mixture is diluted with water and extracted with ether. The combined organic extracts are washed sequentially with water, sodium metabisulfite solution, water and brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give a colorless oil. The oil is chromatographed using silica gel and eluted with methylene chloride to give the title compound as a colorless oil (0.4 g, 34%). Identified by IR and NMR spectral analyses.

Workup

  1. extractionextracted with ether
  2. washThe combined organic extracts are washed sequentially with water, sodium metabisulfite solution, water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customto give a colorless oil
  6. customThe oil is chromatographed
  7. washeluted with methylene chloride

Sources & evidence

ORD record
ord-ad2187ad423a4947b55e7782996bfbfe
Source dataset
uspto-grants-1992_10
Patent number
US05157047

Reaction notes

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