HCID 23503590, compound → HCID 23503603, compound

HRID 1835431Notes

Reaction equation

HRID 1835431 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=[C:5]([CH3:13])[C:4]=1[CH:14]([C:16]1[C:21]([CH3:22])=[CH:20][N:19]=[CH:18][C:17]=1[Br:23])[OH:15]>[O-2].[O-2].[Mn+4].C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=[C:5]([CH3:13])[C:4]=1[C:14]([C:16]1[C:21]([CH3:22])=[CH:20][N:19]=[CH:18][C:17]=1[Br:23])=[O:15]

Participants

4

Reactant 1

HCID 23503590HCID 23503590, compound

Product 1

HCID 23503603HCID 23503603, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

Procedure

3 g of manganese dioxide was added to a toluene (30 ml) solution of 0.43 g (1.1 mmol) of (2,3,4-trimethoxy-6-methylphenyl)(3-bromo-5-methyl-4-pyridyl)methanol obtained in step (b), followed by stirring under reflux by heating for 2 hours. The mixture was subjected to filtration, the solvent was distilled off under reduced pressure, and the crude product thus obtained was purified by silica gel column chromatography to obtain 0.23 g (yield 54%) of 4-(2,3,4-trimethoxy-6-methylbenzoyl)-3-bromo-5-methylpyridine (compound No. 228; m.p. 88-93° C.).

Workup

  1. temperatureunder reflux
  2. temperatureby heating for 2 hours
  3. filtrationThe mixture was subjected to filtration
  4. distillationthe solvent was distilled off under reduced pressure
  5. customthe crude product thus obtained
  6. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1c2789fc8e5b42d89cd7f69f6312a11f
Source dataset
uspto-grants-2004_08
Patent number
US06770662B2

Reaction notes

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