Potassium Hydroxide → HCID 86687552, compound

HRID 1473497Notes

Reaction equation

HRID 1473497 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]([C:12]3[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][C:13]=3[O:22][CH3:23])[O:7][C:8]2=[O:11])=[CH:4][CH:3]=1.[OH-].[K+].[Mn]([O-])(=O)(=O)=[O:27].[K+]>N1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:6](=[O:7])[C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:19])([F:21])[F:20])=[CH:14][C:13]=2[O:22][CH3:23])=[C:9]([CH:10]=1)[C:8]([OH:27])=[O:11]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 516875Potassium PermanganateHCID 86687551HCID 86687551, compound

Product 1

HCID 86687552HCID 86687552, compoundYield 100.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred mixture of 6-bromo-3-(2-methoxy-4-(trifluoromethyl)phenyl)isobenzofuran-1(3H)-one (2.06 g, 5.32 mmol) in KOH (21.3 mL, 5.32 mmol, 25% aqueous solution) and pyridine (10.6 mL) in a pressure tube was added powder potassium permanganate (1.26 g, 7.98 mmol). The reaction was heated at 100° C. After 4 h, the reaction was cooled to RT and the mixture was filtered, and the residue was washed with water. The filtrate was acidified with concentrated HCl until a pH of about 2. The white solid that precipitated out of the solution was filtered off with the aid of water and dried to afford 5-bromo-2-(2-methoxy-4-(trifluoromethyl)benzoyl)benzoic acid (2.16 g, 100% yield). This material was carried on to the next step. m/z (ESI) 405.0 (M+H)+.

Workup

  1. temperaturethe reaction was cooled to RT
  2. filtrationthe mixture was filtered
  3. washthe residue was washed with water
  4. customThe white solid that precipitated out of the solution
  5. filtrationwas filtered off with the aid of water
  6. customdried

Sources & evidence

ORD record
ord-c19bebc219274814a625d44b3e77147d
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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