4-Bromotoluene → HCID 23335289, compound

HRID 903853Notes

Reaction equation

HRID 903853 reaction equation
[K].[OH:2][C:3]1[CH:4]=[CH:5][C:6]([CH3:9])=[N:7][CH:8]=1.Br[C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=1>CN(C)C=O.CO.[Cu]>[CH3:17][C:14]1[CH:15]=[CH:16][C:11]([O:2][C:3]2[CH:4]=[CH:5][C:6]([CH3:9])=[N:7][CH:8]=2)=[CH:12][CH:13]=1

Participants

7

Reactant 3

HCID 78054-BromotolueneHCID 142752-Methyl-5-hydroxypyridineHCID 5462222Potassium

Product 1

HCID 23335289HCID 23335289, compound

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

7.4 g of a potassium salt of 5-hydroxy-2-methylpyridine, 8.5 g of p-bromotoluene and 500 mg of a copper powder were suspended in 25 ml of dimethylformamide, and the mixture was allowed to react in a nitrogen gas stream at 130° C. for 14 hours under stirring. The reaction mixture was diluted with 70 ml of methanol and filtered. The filtrate was immediately concentrated, and to the residue was added 150 ml of chloroform. The mixture was washed with 100 ml of a 0.01 N aqueous sodium hydroxide solution, whereby the unreacted 5-hydroxy-2-methylpyridine shifted to the aqueous layer. The chloroform layer was washed with water, dried with anhydrous sodium sulfate and immediately dried to obtain 8.9 g of oily 5-(p-methylphenoxy)-2-methylpyridine.

Workup

  1. customto react in a nitrogen gas stream at 130° C. for 14 hours
  2. filtrationfiltered
  3. concentrationThe filtrate was immediately concentrated
  4. additionto the residue was added 150 ml of chloroform
  5. washThe mixture was washed with 100 ml of a 0.01 N aqueous sodium hydroxide solution, whereby the unreacted 5-hydroxy-2-methylpyridine
  6. washThe chloroform layer was washed with water
  7. dry with materialdried with anhydrous sodium sulfate
  8. customimmediately dried

Sources & evidence

ORD record
ord-4537c3a2febe4abf93d8f16ad5204662
Source dataset
uspto-grants-1980_10
Patent number
US04229448

Reaction notes

Loading…