Hydrogen Peroxide → HCID 67011838, compound

HRID 912561Notes

Reaction equation

HRID 912561 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH3:13])=[CH:11][C:10]([CH:14]=[O:15])=[C:9]2[CH3:16])=[C:4]([C:17]([F:20])([F:19])[F:18])[CH:3]=1.[O-:21][Mn](=O)(=O)=O.[K+].OO>CC(C)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH3:13])=[CH:11][C:10]([C:14]([OH:21])=[O:15])=[C:9]2[CH3:16])=[C:4]([C:17]([F:20])([F:18])[F:19])[CH:3]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 516875Potassium PermanganateHCID 59807520HCID 59807520, compound

Product 1

HCID 67011838HCID 67011838, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 1-[4-fluoro-2-(trifluoromethyl)phenyl]-2,5-dimethyl-1H-pyrrole-3-carbaldehyde (1.5 g, 5.3 mmol) in acetone (150 mL) was added a 0.3 M solution of KMnO4 (150 mL). The reaction mixture was stirred 3h at room temperature and then was charged with 10% H2O2 (5 mL). After 15 minutes the reaction mixture was filtered and the filtrate was concentrated in vacuo to remove acetone. The remaining aqueous suspension was acidified with acetic acid. The precipitates were recovered by filtration and dried under high vacuum to afford 1-(4-fluoro-2-(trifluoromethyl)phenyl]-2,5-dimethyl-1H-pyrrole-3-carboxylic acid (0.99 g, 62%) as a faintly yellow powder; 1H NMR (CDCl3): δ 7.56 (dd, J=8, 3 Hz, 1H), 7.41 (m, 1H), 7.27 (dd, J=5, 8 Hz, 1H), 6.42 (s, 1H), 2.21 (s, 3H), 1.90 (s, 3H); MS (ESI) m/z 302 [M+H]+.

Workup

  1. filtrationAfter 15 minutes the reaction mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customto remove acetone
  4. filtrationThe precipitates were recovered by filtration
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-3cb0c00099e44eaa95f1e386bbf20509
Source dataset
uspto-grants-2011_09
Patent number
US08026237B2

Reaction notes

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