1-Bromo-2-chlorobenzene → 5-(4-Chlorophenoxy)-2-methylpyridine

HRID 903852Notes

Reaction equation

HRID 903852 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][C:15]([O:2][C:3]2[CH:4]=[CH:5][C:6]([CH3:9])=[N:7][CH:8]=2)=[CH:16][CH:11]=1

Participants

7

Reactant 3

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

Product 1

HCID 233352855-(4-Chlorophenoxy)-2-methylpyridine

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

7.35 g of a potassium salt of 5-hydroxy-2-methylpyridine was suspended in 20 ml of dimethylformamide, and 9.6 g of bromochlorobenzene and 800 mg of a copper powder were added to the suspension. The reaction was effected at a temperature of 120° C. for a period of 18 hours in a nitrogen stream while stirring. After allowing the reaction mixture to cool, the reaction mixture was diluted with 50 ml of methanol and then filtered. The filtrate was immediately concentrated to dryness, and 200 ml of chloroform and 100 ml of water were added to the dried material, and the mixture adjusted to a pH of 9 with 5 N sodium hydroxide. The insoluble matter was again separated by filtration. The resulting chloroform layer was dried with anhydrous sodium sulfate and immediately concentrated to dryness to obtain 8.2 g of oily 5-(p-chlorophenoxy)-2-methylpyridine. Gas chromatography revealed that the thus-obtained product contained no 5-(p-bromophenoxy)-2-methylpyridine.

Workup

  1. temperatureto cool
  2. filtrationfiltered
  3. concentrationThe filtrate was immediately concentrated to dryness, and 200 ml of chloroform and 100 ml of water
  4. additionwere added to the dried material
  5. customThe insoluble matter was again separated by filtration
  6. dry with materialThe resulting chloroform layer was dried with anhydrous sodium sulfate
  7. concentrationimmediately concentrated to dryness

Sources & evidence

ORD record
ord-59acbd61fd454b489c54afc81051f46e
Source dataset
uspto-grants-1980_10
Patent number
US04229448

Reaction notes

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