Hydroquinone → 4-(3-Chloro-5-(trifluoromethyl)pyridin-2-yl)oxyphenol

HRID 260784Notes

Reaction equation

HRID 260784 reaction equation
[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2].[H-].[Na+].[H][H].Cl[C:14]1[C:19]([Cl:20])=[CH:18][C:17]([C:21]([F:24])([F:23])[F:22])=[CH:16][N:15]=1>CN(C)C=O>[Cl:20][C:19]1[C:14]([O:2][C:1]2[CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=2)=[N:15][CH:16]=[C:17]([C:21]([F:23])([F:22])[F:24])[CH:18]=1

Participants

6

Reactant 4

HCID 785HydroquinoneHCID 24758Sodium hydrideHCID 1122342,3-Dichloro-5-(trifluoromethyl)pyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 97959974-(3-Chloro-5-(trifluoromethyl)pyridin-2-yl)oxyphenolYield 43%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution prepared by dissolving 2.8 g of hydroquinone in 20 ml of N,N-dimethylformamide, 1.39 g of sodium hydride (60% oil-based) was added, slowly, with stirring under ice cooling. After completion of the generation of hydrogen gas from the reaction solution, a solution prepared by dissolving 5 g of 2,3-dichloro-5-trifluoromethylpyridine in 10 ml of N,N-dimethylformamide was added dropwise. After stirring at room temperature for 3 hours, the reaction solution was poured into ice-water, and extracted twice with 200 ml of diethyl ether. Then, the ether layers were combined, washed with water, dried over anhydrous magnesium sulfate and then concentrated to give a crude product. This crude product was subjected to silica gel chromatography to give 2.88 g of 4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenol (yield, 43%).

Workup

  1. customTo a solution prepared
  2. additionwas added
  3. additionwas added dropwise
  4. stirringAfter stirring at room temperature for 3 hours
  5. extractionextracted twice with 200 ml of diethyl ether
  6. washwashed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. customto give a crude product

Sources & evidence

ORD record
ord-394a5d34225d43d294bab193affb31b2
Source dataset
uspto-grants-1996_06
Patent number
US05530015

Reaction notes

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