4-Fluorophenol → HCID 20131576, compound

HRID 845566Notes

Reaction equation

HRID 845566 reaction equation
[C:1]([C:5]1([CH:8]([N:10]2[CH:14]=[N:13][CH:12]=[N:11]2)[F:9])[CH2:7][O:6]1)([CH3:4])([CH3:3])[CH3:2].[F:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1.[K]>COCCOCCOC>[F:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:7][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([OH:6])[CH:8]([F:9])[N:10]2[CH:14]=[N:13][CH:12]=[N:11]2)=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 97324-FluorophenolHCID 5462222PotassiumHCID 20131574HCID 20131574, compound

Product 1

HCID 20131576HCID 20131576, compoundYield 49.1%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

3.0 g of 2-tert.-butyl-2-[(1H-1,2,4-triazol-1-yl)fluoromethyl]-oxirane, 1.7 g of 4-fluorophenol and 0.3 g of potassium p-fluorophenate in 10 ml of diethylene glycol dimethyl ether are stirred at 140° C. for 5 hours. After cooling, the mixture is taken up in ice water and extracted with ethyl acetate. The combined organic phases are washed with water, saturated sodium chloride solution and 2N sodium hydroxide solution and again with saturated sodium chloride solution, dried over sodium sulfate and evaporated. Crystallisation from a 1:4 ether/hexane mixture gives 2.3 g of 1-(4-fluorophenoxy)-2-tert.-butyl-2-hydroxy-3-fluoro-3-(1H-1,2,4-triazol-1-yl)-propane, melting point 89°-90° C.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washThe combined organic phases are washed with water, saturated sodium chloride solution and 2N sodium hydroxide solution and again with saturated sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customCrystallisation from a 1:4 ether/hexane mixture

Sources & evidence

ORD record
ord-0cf6473708a64ccd8605cb6c182a5003
Source dataset
uspto-grants-1988_07
Patent number
US04758670

Reaction notes

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