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

HRID 484232Notes

Reaction equation

HRID 484232 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

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 962WaterSolvent

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-c365aec916644c7a9b5a4d027a92196f
Source dataset
uspto-grants-1993_07
Patent number
US05229524

Reaction notes

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