Water → HCID 13532816, compound

HRID 1982614Notes

Reaction equation

HRID 1982614 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([OH:9])=[C:4]([CH3:10])[CH:3]=1.[F:11][C:12]1[CH:17]=[C:16](F)[CH:15]=[C:14]([F:19])[CH:13]=1.C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O.C1(C)C=CC=CC=1>[F:11][C:12]1[CH:17]=[C:16]([CH:15]=[C:14]([F:19])[CH:13]=1)[O:9][C:5]1[C:6]([CH3:8])=[CH:7][C:2]([NH2:1])=[CH:3][C:4]=1[CH3:10]

Participants

7

Reactant 4

HCID 962WaterHCID 97451,3,5-TrifluorobenzeneHCID 11430Potassium CarbonateHCID 826684-Amino-2,6-dimethylphenol

Product 1

HCID 13532816HCID 13532816, compoundYield 75.6%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 1140TolueneSolvent

Procedure

A mixture of 4-amino-2,6-dimethylphenol (6.92 g), 1,3,5-trifluorobenzene (10.00 g), anhydrous potassium carbonate (13.93 g) and anhydrous cuprous chloride (0.50 g) in dry dimethylsulfoxide (100 ml) was heated under reflux for 4 hours, whereby the inner temperature raised from 120° C. to 150° C. After completion of the reaction, the reaction mixture was cooled to room temperature, and cold water (200 ml) and toluene (100 ml) were added thereto. After continuation of stirring for 30 minutes, the resultant mixture was filtered on celite to remove insoluble materials. The toluene layer was washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography using a mixture of methylene chloride and n-hexane (1:1) as an eluting solvent to give 9.50 g of 4-(3,5-difluorophenoxy)3,5-dimethylaniline as yellowish white crystals. M.P., 67.6° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 hours
  3. temperaturewhereby the inner temperature raised from 120° C. to 150° C
  4. customAfter completion of the reaction
  5. filtrationthe resultant mixture was filtered on celite
  6. customto remove insoluble materials
  7. washThe toluene layer was washed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel chromatography
  11. additiona mixture of methylene chloride and n-hexane (1:1) as an eluting solvent

Sources & evidence

ORD record
ord-a3036559c7a642669e41dae1266ab82c
Source dataset
uspto-grants-1986_06
Patent number
US04596890

Reaction notes

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