2-Methyl-5-hydroxypyridine → HCID 23335279, compound

HRID 903859Notes

Reaction equation

HRID 903859 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][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=1>CN(C)C=O.CO.[Cu]>[F:18][C:17]([F:20])([F:19])[C:14]1[CH:15]=[CH:16][C:11]([O:2][C:3]2[CH:4]=[CH:5][C:6]([CH3:9])=[N:7][CH:8]=2)=[CH:12][CH:13]=1

Participants

7

Reactant 3

HCID 142752-Methyl-5-hydroxypyridineHCID 67872Benzene, 1-bromo-4-(trifluoromethyl)-HCID 5462222Potassium

Product 1

HCID 23335279HCID 23335279, compound

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
125 °C

Procedure

4 g of a potassium salt of 5-hydroxy-2-methylpyridine was suspended in 10 ml of dimethylformamide, and 6.15 g of p-bromobenzotrifluoride and 500 mg of a copper powder were added to the suspension, followed by stirring in a nitrogen stream at 125° C. for 18 hours to effect the reaction. The reaction mixture was allowed to cool, diluted with 50 ml of methanol and then filtered. The filtrate was immediately dried to a solid, and 150 ml of chloroform and 100 ml of water were added to the residue. The resulting mixture was adjusted to a pH of 9.5 with 5 N sodium hydroxide and any insoluble matter again separated by filtration. The chloroform layer was dried with anhydrous sodium sulfate and immediately concentrated to dryness to obtain 5.6 g of oily 5-(p-trifluoromethylphenoxy)-2-methylpyridine.

Workup

  1. customthe reaction
  2. temperatureto cool
  3. filtrationfiltered
  4. dry with materialThe filtrate was immediately dried to a solid, and 150 ml of chloroform and 100 ml of water
  5. additionwere added to the residue
  6. customany insoluble matter again separated by filtration
  7. dry with materialThe chloroform layer was dried with anhydrous sodium sulfate
  8. concentrationimmediately concentrated to dryness

Sources & evidence

ORD record
ord-7a2d47da2026491d883dcbbc29ff1c90
Source dataset
uspto-grants-1980_10
Patent number
US04229448

Reaction notes

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