2-(3-Bromo-4-fluoro-alpha-hydroxybenzyl)-3-methoxymethoxypyridine → 2-(3-Bromo-4-fluorobenzoyl)-3-methoxymethoxypyridine

HRID 442722Notes

Reaction equation

HRID 442722 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[F:20])[CH:5]([C:7]1[C:12]([O:13][CH2:14][O:15][CH3:16])=[CH:11][CH:10]=[CH:9][N:8]=1)[OH:6]>[O-2].[O-2].[Mn+4].C(OCC)(=O)C>[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][CH2:14][O:15][CH3:16])=[CH:11][CH:10]=[CH:9][N:8]=1)=[O:6]

Participants

4

Reactant 1

HCID 539404062-(3-Bromo-4-fluoro-alpha-hydroxybenzyl)-3-methoxymethoxypyridine

Product 1

HCID 539864842-(3-Bromo-4-fluorobenzoyl)-3-methoxymethoxypyridineYield 93.4%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-(3-bromo-4-fluoro-α-hydroxy-benzyl)-3-methoxymethoxypyridine (14.0 g), activated manganese dioxide (41.8 g) and ethyl acetate (200 mL) was stirred overnight at room temperature, which was then subjected to filtration. The filtrate was concentrated under reduced pressure. The concentrate was purified by means of a silica gel column (ethyl acetate--hexane) to afford 2-(3-bromo-4-fluorobenzoyl)-3-methoxymethoxypyridine (13.0 g) (compound B-5). Physical properties and spectrum data of the product are shown in Table 3 and Table 4.

Workup

  1. filtrationwhich was then subjected to filtration
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customThe concentrate was purified by means of a silica gel column (ethyl acetate--hexane)

Sources & evidence

ORD record
ord-7b1ea55e66054eb0abdeaf0b8c370e45
Source dataset
uspto-grants-1999_04
Patent number
US05891895

Reaction notes

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