1,4-Dibromobenzene → 5-(4-Bromophenoxy)-2-methylpyridine

HRID 903854Notes

Reaction equation

HRID 903854 reaction equation
[K].[OH:2][C:3]1[CH:4]=[CH:5][C:6]([CH3:9])=[N:7][CH:8]=1.[Br:10][C:11]1[CH:16]=[CH:15][C:14](Br)=[CH:13][CH:12]=1>CC(N(C)C)=O.CO>[Br:10][C:11]1[CH:16]=[CH:15][C:14]([O:2][C:3]2[CH:4]=[CH:5][C:6]([CH3:9])=[N:7][CH:8]=2)=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 78041,4-DibromobenzeneHCID 142752-Methyl-5-hydroxypyridineHCID 5462222Potassium

Product 1

HCID 233352765-(4-Bromophenoxy)-2-methylpyridine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 31374DimethylacetamideSolvent

Procedure

2.84 g of a potassium salt of 5-hydroxy-2-methylpyridine, 4.7 g of p-dibromobenzene and 400 mg of cuprous oxide were suspended in 10 ml of dimethylacetamide, and the mixture was allowed to react in a nitrogen gas stream at 150° C. for 15 hours. The reaction mixture was diluted with 30 ml of methanol and then filtered. The filtrate was immediately dried, and the residue was taken into 100 ml of chloroform and washed successively with a 3% aqueous sodium carbonate solution and 50 ml of water. The chloroform layer was dried with anhydrous sodium sulfate and immediately concentrated to dryness to obtain 2.1 g of oily 5-(p-bromophenoxy)-2-methylpyridine.

Workup

  1. customto react in a nitrogen gas stream at 150° C. for 15 hours
  2. filtrationfiltered
  3. customThe filtrate was immediately dried
  4. washwashed successively with a 3% aqueous sodium carbonate solution and 50 ml of water
  5. dry with materialThe chloroform layer was dried with anhydrous sodium sulfate
  6. concentrationimmediately concentrated to dryness

Sources & evidence

ORD record
ord-0b5c483a0c4a419f86c81377d9cbecb7
Source dataset
uspto-grants-1980_10
Patent number
US04229448

Reaction notes

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