Benzene, 1-bromo-3-(trifluoromethyl)- → HCID 23335287, compound

HRID 903855Notes

Reaction equation

HRID 903855 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]([C:17]([F:20])([F:19])[F:18])[CH:14]=[CH:15][CH:16]=1>CN(C)C=O.CC(C)=O.[Cu]>[F:18][C:17]([F:20])([F:19])[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 9817Benzene, 1-bromo-3-(trifluoromethyl)-HCID 142752-Methyl-5-hydroxypyridineHCID 5462222Potassium

Product 1

HCID 23335287HCID 23335287, compound

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

3.68 g of a potassium salt of 5-hydroxy-2-methylpyridine was suspended in 10 ml of dimethylformamide, and 5.65 g of m-bromobenzotrifluoride and 300 mg of copper powders were added to the suspension, followed by allowing the mixture to react in a nitrogen stream at 120° C. for 15 hours while stirring. After cooling, the reaction mixture was diluted with 40 ml of acetone and filtered. The filtrate was immediately dried to solidify, and 100 ml of chloroform and 50 ml of water were added thereto. The mixture was adjusted to a pH of 9 with 5 N sodium hydroxide, and any insoluble matter was again separated by filtration. The resulting chloroform layer was dried with anhydrous sodium sulfate and immediately concentrated to dryness to obtain 4.1 g of oily 5-(m-trifluoromethylphenoxy)-2-methylpyridine.

Workup

  1. customto react in a nitrogen stream at 120° C. for 15 hours
  2. temperatureAfter cooling
  3. filtrationfiltered
  4. customThe filtrate was immediately dried
  5. addition100 ml of chloroform and 50 ml of water were added
  6. customany insoluble matter was again separated by filtration
  7. dry with materialThe resulting chloroform layer was dried with anhydrous sodium sulfate
  8. concentrationimmediately concentrated to dryness

Sources & evidence

ORD record
ord-7575242b326e478c8403a225747e6fa5
Source dataset
uspto-grants-1980_10
Patent number
US04229448

Reaction notes

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