Pyridine → HCID 69140603, compound

HRID 1473648Notes

Reaction equation

HRID 1473648 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[O:18][CH3:19])[O:7][C:8]2=[O:11])=[CH:4][CH:3]=1.[OH-].[K+].N1C=CC=CC=1.[Mn]([O-])(=O)(=O)=[O:29].[K+]>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:6](=[O:29])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][CH3:19])=[C:9]([CH:10]=1)[C:8]([OH:7])=[O:11]

Participants

5

Reactant 4

HCID 1049PyridineHCID 14797Potassium HydroxideHCID 516875Potassium PermanganateHCID 86687719HCID 86687719, compound

Product 1

HCID 69140603HCID 69140603, compoundYield 78%

Conditions

Temperature
100 °C

Procedure

This compound was prepared according to Ukita et al J. Med. Chem. 2001, 44, 2204. To a stirred mixture of 6-bromo-3-(2-methoxyphenyl)isobenzofuran-1(3H)-one (5.15 g, 16.1 mmol) in KOH (25% aqueous) (64.5 mL, 16.1 mmol) and pyridine (32.3 mL, 16.1 mmol) in a pressure tube was added powder potassium permanganate (3.83 g, 24.2 mmol). The reaction was heated at 100° C. After 4 h, LCMS showed ˜95% conversion to product. The reaction was cooled to rt. The mixture was filtered, and the solid residue was washed with water. The filtrate was acidified with concentrated HCl until pH=2. A sticky white solid was filtered off with the aid of water and dried to afford 5-bromo-2-(2-methoxybenzoyl)benzoic acid (4.2 g, 78% yield). m/z (ESI) 335.0 (M+H)+, 337.0 (M+3H)+.

Workup

  1. customThis compound was prepared
  2. temperatureThe reaction was cooled to rt
  3. filtrationThe mixture was filtered
  4. washthe solid residue was washed with water
  5. filtrationA sticky white solid was filtered off with the aid of water
  6. customdried

Sources & evidence

ORD record
ord-408b8c5d6acb4746bcb338c9518a63be
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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