Acetone → 2-(3-Bromo-4-fluorobenzoyl)-3-hydroxypyridine

HRID 442725Notes

Reaction equation

HRID 442725 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[F:20])[C:5]([C:7]1[C:12]([O:13]COC)=[CH:11][CH:10]=[CH:9][N:8]=1)=[O:6].S(=O)(=O)(O)O.CC(C)=O.[OH-].[Na+]>O>[Br:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[F:20])[C:5]([C:7]1[C:12]([OH:13])=[CH:11][CH:10]=[CH:9][N:8]=1)=[O:6]

Participants

6

Reactant 4

HCID 180AcetoneHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 539864842-(3-Bromo-4-fluorobenzoyl)-3-methoxymethoxypyridine

Product 1

HCID 539533172-(3-Bromo-4-fluorobenzoyl)-3-hydroxypyridineYield 91.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-(3-bromo-4-fluorobenzoyl)-3-methoxymethoxypyridine (5.68 g), 3.6N-sulfuric acid (6.0 mL) and acetone (30 mL) was refluxed for 3 hours. The reaction mixture was then poured into water, neutralized with a saturated aqueous solution of sodium hydroxide, and extracted with ethyl acetate. The extract was washed with water and a saturated aqueous saline solution, successively, and dried (sodium sulfate) and then concentrated. The concentrate was purified by means of a silica gel column (ethyl acetate--hexane) to afford 2-(3-bromo-4-fluorobenzoyl)-3-hydroxypyridine (4.51 g) (compound C-5). Physical properties and spectrum date of the product are shown in Table 5 and Table 6.

Workup

  1. temperaturewas refluxed for 3 hours
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materiala saturated aqueous saline solution, successively, and dried (sodium sulfate)
  5. concentrationconcentrated
  6. customThe concentrate was purified by means of a silica gel column (ethyl acetate--hexane)

Sources & evidence

ORD record
ord-619767b40a284e0997c1827e2daef30e
Source dataset
uspto-grants-1999_04
Patent number
US05891895

Reaction notes

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