1-Bromo-3-chlorobenzene → HCID 23335278, compound

HRID 903856Notes

Reaction equation

HRID 903856 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:12]=[C:13]([Cl:17])[CH:14]=[CH:15][CH:16]=1>CN(C)C=O.C(O)C.[Cu]>[Cl:17][C:13]1[CH:12]=[C:11]([CH:16]=[CH:15][CH:14]=1)[O:2][C:3]1[CH:4]=[CH:5][C:6]([CH3:9])=[N:7][CH:8]=1

Participants

7

Reactant 3

HCID 79281-Bromo-3-chlorobenzeneHCID 142752-Methyl-5-hydroxypyridineHCID 5462222Potassium

Product 1

HCID 23335278HCID 23335278, compound

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

3 g of a potassium salt of 5-hydroxy-2-methylpyridine, 3.83 g of m-bromochlorobenzene and 200 mg of a copper powder were suspended in 8 ml of dimethylformamide, followed by allowing the mixture to react in a nitrogen gas stream at 130° C. for 13 hours while stirring. The reaction mixture was diluted with 40 ml of ethanol and filtered. The filtrate was immediately concentrated, and 80 ml of chloroform was added to the residue. The mixture was washed with a 0.01 N aqueous sodium hydroxide solution. The chloroform layer was washed with water, dried with anhydrous sodium sulfate and dried to solidify to obtain 2.96 g of oily 5-(m-chlorophenoxy)-2-methylpyridine.

Workup

  1. customto react in a nitrogen gas stream at 130° C. for 13 hours
  2. filtrationfiltered
  3. concentrationThe filtrate was immediately concentrated
  4. addition80 ml of chloroform was added to the residue
  5. washThe mixture was washed with a 0.01 N aqueous sodium hydroxide solution
  6. washThe chloroform layer was washed with water
  7. dry with materialdried with anhydrous sodium sulfate
  8. customdried

Sources & evidence

ORD record
ord-a716f55957bf49fb8df6084c78376103
Source dataset
uspto-grants-1980_10
Patent number
US04229448

Reaction notes

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