4-Bromoanisole → HCID 23335283, compound

HRID 903857Notes

Reaction equation

HRID 903857 reaction equation
[K].[OH:2][C:3]1[CH:4]=[CH:5][C:6]([CH3:9])=[N:7][CH:8]=1.[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15](Br)=[CH:14][CH:13]=1>CC(N(C)C)=O.CO.[Cu]>[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([O:2][C:3]2[CH:4]=[CH:5][C:6]([CH3:9])=[N:7][CH:8]=2)=[CH:14][CH:13]=1

Participants

7

Reactant 3

HCID 77304-BromoanisoleHCID 142752-Methyl-5-hydroxypyridineHCID 5462222Potassium

Product 1

HCID 23335283HCID 23335283, compound

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 887MethanolSolventHCID 31374DimethylacetamideSolvent

Procedure

4 g of a potassium salt of 5-hydroxy-2-methylpyridine was suspended in 10 ml of dimethylacetamide, and 5.1 g of p-methoxybromobenzene and 450 mg of a copper powder were added to the suspension, followed by allowing the mixture to react in a nitrogen stream at 140° C. for 14 hours. The reaction mixture was diluted with 50 ml of methanol and filtered, and the filtrate was immediately dried to a solid. 100 ml of ethyl acetate was added to the residue, and the mixture was washed with 50 ml of an aqueous sodium hydroxide solution at pH 9. The ethyl acetate layer was washed with water, dried with anhydrous sodium sulfate and immediately dried to obtain 3.9 g of oily 5-(p-methoxyphenoxy)-2-methylpyridine.

Workup

  1. customto react in a nitrogen stream at 140° C. for 14 hours
  2. filtrationfiltered
  3. customthe filtrate was immediately dried to a solid
  4. addition100 ml of ethyl acetate was added to the residue
  5. washthe mixture was washed with 50 ml of an aqueous sodium hydroxide solution at pH 9
  6. washThe ethyl acetate layer was washed with water
  7. dry with materialdried with anhydrous sodium sulfate
  8. customimmediately dried

Sources & evidence

ORD record
ord-44b688a30279464a8bd6638c4bbf2c6b
Source dataset
uspto-grants-1980_10
Patent number
US04229448

Reaction notes

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