Hydrogen Peroxide → HCID 67011838, compound

HRID 383730Notes

Reaction equation

HRID 383730 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 3 h 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]+. To a suspension of 1-(4-fluoro-2-(trifluoromethyl)phenyl]-2,5-dimethyl-1H-pyrrole-3-carboxylic acid (0.65 g, 2.16 mmol) in anhyd toluene (5.0 mL) cooled to 0-3° C. were added thionyl chloride (0.25 mL) and DMF (20 μL). The reaction mixture was allowed to warm to room temperature where it remained for 3 h and then was concentrated in vacuo. The residue was evaporated twice from 5 mL of toluene to remove thionyl chloride and then was triturated in 3 mL of hexanes. The solids were removed by filtration and the filtrate was concentrated under reduced pressure and dried under high vacuum to afford the title compound (0.44 g, 64%) as a pale brown solid; 1H NMR (CDCl3): δ 7.59 (dd, J=8, 3 Hz, 1H), 7.44 (m, 1H), 7.27 (dd, J=5, 8 Hz, 1H), 6.51 (s, 1H), 2.17 (s, 3H), 1.89 (s, 3H); MS (ESI) m/z 320 [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-93468dfc2c9849f99e092736212c89ce
Source dataset
uspto-grants-2013_02
Patent number
US08367667B2

Reaction notes

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