2-(3-Bromo-alpha-hydroxybenzyl)-3-methoxymethoxypyridine 1-oxide → 2-(3-Bromobenzoyl)-3-methoxymethoxy pyridine 1-oxide

HRID 442727Notes

Reaction equation

HRID 442727 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[CH:5]([C:7]1[C:12]([O:13][CH2:14][O:15][CH3:16])=[CH:11][CH:10]=[CH:9][N+:8]=1[O-:17])[OH:6]>C(OCC)(=O)C.[O-2].[O-2].[Mn+4]>[Br:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[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-:17])=[O:6]

Participants

4

Reactant 1

HCID 542239762-(3-Bromo-alpha-hydroxybenzyl)-3-methoxymethoxypyridine 1-oxide

Product 1

HCID 544656892-(3-Bromobenzoyl)-3-methoxymethoxy pyridine 1-oxideYield 94.2%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 2-(3-bromo-α-hydroxybenzyl)-3-methoxymethoxypyridine 1-oxide (4.58 g) and activated manganese dioxide (13.1 g) in ethyl acetate (150 mL) was stirred overnight at room temperature. The reaction mixture was subjected to filtration, and 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-bromobenzoyl)-3-methoxymethoxy pyridine 1-oxide (4.29 g). Physical properties and spectrum data of the product are shown below:

Workup

  1. filtrationThe reaction mixture was 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-d13c71dc392b4491977924931e22e7da
Source dataset
uspto-grants-1999_04
Patent number
US05891895

Reaction notes

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