1-Bromo-2-chlorobenzene → 5-(2-Chlorophenoxy)-2-methylpyridine

HRID 903858Notes

Reaction equation

HRID 903858 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][CH:14]=[CH:13][C:12]=1[Cl:17]>CN(C)C=O.CO.[Cu]>[Cl:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[O:2][C:3]1[CH:4]=[CH:5][C:6]([CH3:9])=[N:7][CH:8]=1

Participants

7

Reactant 3

HCID 127541-Bromo-2-chlorobenzeneHCID 142752-Methyl-5-hydroxypyridineHCID 5462222Potassium

Product 1

HCID 233352845-(2-Chlorophenoxy)-2-methylpyridine

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

4 g of a potassium salt of 5-hydroxy-2-methylpyridine, 5.2 g of o-bromochlorobenzene and 250 mg of a copper powder were suspended in 10 ml of dimethylformamide, and the mixture was allowed to react in a nitrogen gas stream at 115° C. for 23 hours under stirring. The reaction mixture was diluted with 70 ml of methanol and filtered. The filtrate was dried to a solid, and 120 ml of chloroform was added to the residue. The mixture was washed with 70 ml of an aqueous sodium hydroxide solution at pH of 9. The solvent layer was washed with water, dried with anhydrous sodium sulfate and immediately dried to obtain 2.8 g of oily 5-(o-chlorophenoxy)-2-methylpyridine.

Workup

  1. customto react in a nitrogen gas stream at 115° C. for 23 hours
  2. filtrationfiltered
  3. dry with materialThe filtrate was dried to a solid, and 120 ml of chloroform
  4. additionwas added to the residue
  5. washThe mixture was washed with 70 ml of an aqueous sodium hydroxide solution at pH of 9
  6. washThe solvent layer was washed with water
  7. dry with materialdried with anhydrous sodium sulfate
  8. customimmediately dried

Sources & evidence

ORD record
ord-7481af54664c4ea28e0bfeed31917260
Source dataset
uspto-grants-1980_10
Patent number
US04229448

Reaction notes

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