2-(3-Bromo-alpha-hydroxybenzyl)-3-methoxymethoxypyridine → 2-(3-Bromobenzoyl)-3-methoxymethoxypyridine

HRID 442721Notes

Reaction equation

HRID 442721 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=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)[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][CH:19]=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:6]

Participants

4

Reactant 1

HCID 543301292-(3-Bromo-alpha-hydroxybenzyl)-3-methoxymethoxypyridine

Product 1

HCID 539766302-(3-Bromobenzoyl)-3-methoxymethoxypyridineYield 86.9%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-(3-bromo-α-hydroxybenzyl)-3-methoxymethoxypyridine (6.43 g), activated manganese dioxide (18.4 g) and ethyl acetate (50 mL) was stirred overnight at room temperature, which was then subjected to filtration. The filtrate was subjected to concentration under reduced pressure. The concentrate was purified by means of a silica gel column (ethyl acetate--hexane) to afford 2-(3-bromobenzoyl)-3-methoxymethoxypyridine (5.55 g) (compound B-1). Physical properties and spectrum data of the product are shown in Table 3 and Table 4. In substantially the same manner as above, compounds B-2 to B-4, B-7 and B-8 shown in Table 3 were produced.

Workup

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

Sources & evidence

ORD record
ord-55464c84364e43b584f8ff559c59ce7c
Source dataset
uspto-grants-1999_04
Patent number
US05891895

Reaction notes

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