(2,3,4-Trimethoxy-6-methylphenyl)(5-bromo-4-chloro-2-methoxy-3-pyridyl)methanol → 3-(2,3,4-Trimethoxy-6-methylbenzoyl)-5-bromo-4-chloro-2-methoxypyridine

HRID 243769Notes

Reaction equation

HRID 243769 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:17]([O:24][CH3:25])=[N:18][CH:19]=[C:20]([Br:23])[C:21]=1[Cl:22])[OH:15]>C1(C)C=CC=CC=1.[O-2].[O-2].[Mn+4]>[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:17]([O:24][CH3:25])=[N:18][CH:19]=[C:20]([Br:23])[C:21]=1[Cl:22])=[O:15]

Participants

4

Reactant 1

HCID 23082647(2,3,4-Trimethoxy-6-methylphenyl)(5-bromo-4-chloro-2-methoxy-3-pyridyl)methanol

Product 1

HCID 112626853-(2,3,4-Trimethoxy-6-methylbenzoyl)-5-bromo-4-chloro-2-methoxypyridineYield 87%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst2×HCID 1140TolueneSolvent

Procedure

4.55 g of manganese dioxide (88%, 46 mmol) was added to a solution having 2.21 g (5.1 mmol) of (2,3,4-trimethoxy-6-methylphenyl)(5-bromo-4-chloro-2-methoxy-3-pyridyl)methanol dissolved in 70 ml of toluene, followed by reflux with heating for 1 hour. 4.55 g of manganese dioxide (88%, 46 mmol) was further added, followed by reflux with heating for 1 hours. The reaction mixture was cooled to room temperature, manganese dioxide was removed by filtration on the pad of celite, and toluene was distilled off under reduced pressure. The obtained crude product was purified by silica gel chromatography to obtain 1.90 g (yield: 87%) of 3-(2,3,4-trimethoxy-6-methylbenzoyl)-5-bromo-4-chloro-2-methoxypyridine (melting point 84 to 87° C.).

Workup

  1. temperatureby reflux
  2. temperaturewith heating for 1 hour
  3. temperatureby reflux
  4. temperaturewith heating for 1 hours
  5. custommanganese dioxide was removed by filtration on the pad of celite, and toluene
  6. distillationwas distilled off under reduced pressure
  7. customThe obtained crude product
  8. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-c72d574868434ab6bf059f7578377838
Source dataset
uspto-grants-2014_02
Patent number
US08653277B2

Reaction notes

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