2-Bromo-6-methylpyridine → HCID 23157489, compound

HRID 273383Notes

Reaction equation

HRID 273383 reaction equation
[Na].[Br:2][C:3]1[C:8]([CH3:9])=[CH:7][C:6]([OH:10])=[CH:5][C:4]=1[CH3:11].Br[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[N:14]=1>C(OCC)(=O)C.[Cu]>[Br:2][C:3]1[C:8]([CH3:9])=[CH:7][C:6]([O:10][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[N:14]=2)=[CH:5][C:4]=1[CH3:11]

Participants

5

Reactant 2

HCID 792052-Bromo-6-methylpyridineHCID 68720392HCID 68720392, compound

Product 1

HCID 23157489HCID 23157489, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
185 °C

Procedure

To a solution of sodium hydroxide (0.23 g, 5.81 mmol) in methanol (50 mL) was added 4-bromo-3,5-dimethylphenol (1.17 g, 5.81 mmol) and the mixture was left standing at room temperature for 10 min. and concentrated to dryness to give 4-bromo-3,5-dimethylphenol sodium salt (1.30 g). Then, a mixture of the obtained 4-bromo-3,5-dimethylphenol sodium salt (1.30 g), 2-bromo-6-methylpyridine (1.0 g, 5.81 mmol) and copper powder (11 mg, 0.17 mmol) was stirred at 185° C. for 1 hr. The reaction mixture was cooled, diluted with ethyl acetate, washed with water and saturated brine, dried and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-hexane/ethyl acetate=5/1) to give the title compound (1.25 g, yield 74%) as a pale-yellow oil.

Workup

  1. temperatureThe reaction mixture was cooled
  2. washwashed with water and saturated brine
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane-hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-a252f2dc7791448b85a51f9de5216d3f
Source dataset
uspto-grants-2008_11
Patent number
US07456218B2

Reaction notes

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