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Acetic Acid → 3-Bromo-2-(4-chlorophenyl)-4,5-bis(trifluoromethyl)-1H-pyrrole

HRID 1198736
Notes
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Reaction equation

HRID 1198736 reaction equation
[Br:1]Br.[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[NH:14][C:13]([C:15]([F:18])([F:17])[F:16])=[C:12]([C:19]([F:22])([F:21])[F:20])[CH:11]=2)=[CH:6][CH:5]=1.C(O)(=O)C.C([O-])(=O)C.[Na+]>O>[Br:1][C:11]1[C:12]([C:19]([F:22])([F:20])[F:21])=[C:13]([C:15]([F:16])([F:17])[F:18])[NH:14][C:10]=1[C:7]1[CH:6]=[CH:5][C:4]([Cl:3])=[CH:9][CH:8]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 24408BromineHCID 517045Sodium AcetateHCID 19103181HCID 19103181, compound

Product 1

HCID 191031693-Bromo-2-(4-chlorophenyl)-4,5-bis(trifluoromethyl)-1H-pyrroleYield 65.4%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Procedure

Bromine (0.527 g, 3.3 mmol) is added to a room temperature solution of 5-(p-chlorophenyl)-2,3-bis(trifluoromethyl)pyrrole (0.94 g, 3.0 mmol), acetic acid (5 mL) and sodium acetate (0.492 g, 6 mmol). After stirring for 2 hours 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 magnesium sulfate and concentrated in vacuo to obtain a solid. Crystallization of the solid from hexanes gives the title product as white crystals (0.77 g, mp 64.5°-65.0° C., 65%).

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 magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customto obtain a solid
  6. customCrystallization of the solid from hexanes

Sources & evidence

ORD record
ord-18c121f2dafb494483be4acd52a9f0b8
Source dataset
uspto-grants-1994_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05281719

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes