3-(Trifluoromethyl)phenol → 3-Chloro-2-(3-(trifluoromethyl)phenoxy)pyridine

HRID 582253

Reaction equation

HRID 582253 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.Cl[C:13]1[C:18]([Cl:19])=[CH:17][CH:16]=[CH:15][N:14]=1>CN(C)C=O>[Cl:19][C:18]1[C:13]([O:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:10])([F:11])[F:1])[CH:4]=2)=[N:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 73763-(Trifluoromethyl)phenolHCID 169882,3-Dichloropyridine

Product 1

HCID 180084773-Chloro-2-(3-(trifluoromethyl)phenoxy)pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

7.68 g of sodium hydride dispersion (ca. 50 percent in mineral oil) was washed with pentane under nitrogen and 100 ml of N,N-dimethylformamide was then added. 21.92 g (135 mmol) of 3-(trifluoromethyl)phenol was added dropwise over 30 minutes at room temperature. The resultant phenate solution was added dropwise over 2 hours, under nitrogen, to a solution of 20.1 g (136 mmol) of 2,3-dichloropyridine in 80 ml of N,N-dimethylformamide, heated to 120° C. After a reaction time of 3 hours, the mixture was cooled to room temperature, the precipitate of sodium chloride was filtered off and the filtrate was concentrated. The residue was extracted with toluene and 0.1 N hydrochloric acid and the organic phase was washed with saturated sodium chloride solution and concentrated. The oily residue was distilled under vacuum. The yield of the title compound was 24.75 g (67 percent) of a colorless oil, content (GC) 99.7 percent. Other data concerning the title compound was:

Workup

  1. wash7.68 g of sodium hydride dispersion (ca. 50 percent in mineral oil) was washed with pentane under nitrogen
  2. addition100 ml of N,N-dimethylformamide was then added
  3. temperatureAfter a reaction time of 3 hours, the mixture was cooled to room temperature
  4. filtrationthe precipitate of sodium chloride was filtered off
  5. concentrationthe filtrate was concentrated
  6. extractionThe residue was extracted with toluene and 0.1 N hydrochloric acid
  7. washthe organic phase was washed with saturated sodium chloride solution
  8. concentrationconcentrated
  9. distillationThe oily residue was distilled under vacuum

Sources & evidence

ORD record
ord-72c881243ff344f29b5021aa5ecadaa6
Source dataset
uspto-grants-1999_07
Patent number
US05922870

Linked notes

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