Hydrochloric Acid → 4-{[3-Fluoro-5-(trifluoromethyl)pyridin-2-yl]oxy}phenol

HRID 1762395Notes

Reaction equation

HRID 1762395 reaction equation
[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2].[OH-].[K+].F[C:12]1[C:17]([F:18])=[CH:16][C:15]([C:19]([F:22])([F:21])[F:20])=[CH:14][N:13]=1.Cl>CS(C)=O>[F:18][C:17]1[C:12]([O:2][C:1]2[CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=2)=[N:13][CH:14]=[C:15]([C:19]([F:21])([F:20])[F:22])[CH:16]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 785HydroquinoneHCID 14797Potassium HydroxideHCID 134215472,3-Difluoro-5-(trifluoromethyl)pyridine

Product 1

HCID 155928354-{[3-Fluoro-5-(trifluoromethyl)pyridin-2-yl]oxy}phenolYield 71%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A mixture of 16.5 g (0.15 mol) of hydroquinone, 19.1 g (0.3 mol) of potassium hydroxide (88%) in 600 ml of dimethylsulfoxide is stirred at room temperature under a nitrogen atmosphere until everything is dissolved. A solution of 13.7 g (0.075 mol) of 2,3-difluoro-5-trifluoromethyl-pyridine in 25 ml of dimethylsulfoxide is added dropwise at a temperature of 15°-20°. The reaction mixture is then stirred at room temperature for 24 hours. Then it is poured into ice/water and the mixture is acidified with hydrochloric acid, extracted with methylene chloride, washed with water, dried over magnesium sulfate, filtered and evaporated to dryness. The residue crystallizes in hexane/ethyl acetate to yield 14.5 g (71%) of white crystals, melting at 97°.

Workup

  1. dissolutionis dissolved
  2. stirringThe reaction mixture is then stirred at room temperature for 24 hours
  3. extractionextracted with methylene chloride
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe residue crystallizes in hexane/ethyl acetate

Sources & evidence

ORD record
ord-d4184ff40eba4ae4818915b994f89a7b
Source dataset
uspto-grants-1989_05
Patent number
US04832736

Reaction notes

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