Water → 1-Methyl-2-(propylsulfanyl)-4-[3-(trifluoromethyl)phenoxy]benzene

HRID 372460Notes

Reaction equation

HRID 372460 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[S:9][CH2:10][CH2:11][CH3:12].[OH-].[K+].Br[C:16]1[CH:17]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:19]=[CH:20][CH:21]=1.O>CN(C)C(=O)C>[F:23][C:22]([F:25])([F:24])[C:18]1[CH:17]=[C:16]([O:8][C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[C:3]([S:9][CH2:10][CH2:11][CH3:12])[CH:4]=2)[CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 9817Benzene, 1-bromo-3-(trifluoromethyl)-HCID 14797Potassium HydroxideHCID 144045044-Methyl-3-(propylsulfanyl)phenol

Product 1

HCID 203277371-Methyl-2-(propylsulfanyl)-4-[3-(trifluoromethyl)phenoxy]benzene

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

4-Methyl-3-(n-propylthio)phenol (8.4 g, 0.05 mole) and 85.5 % potassium hydroxide (3.3 g, 0.05 mole) were dissolved in N,N-dimethylacetamide (50 ml) above 90° C. 3-Bromotrifluoromethylbenzene (11.2 g, 0.05 mole) and Cu powder (0.5 g, 0.008 mole) were added to this solution below 90° C and the mixture was stirred at 110°-160° C for 14 hr. After cooling, the reaction mixture was poured into water (150 ml) and extracted twice benzene. The combined organic layers were washed with 5 % sodium hydroxide solution, 5 % hydrochloric acid solution, and water, then dried over sodium fulfate. The solvent was removed, and the residue was purified by column chromatography on silica gel using n-hexane benzene (2 : 1). The yield of 4-methyl-3-n-propylthiophenyl 3-trifluoromethylphenyl ether was 8.9 g (54.8 %), colorless oil, nD25 1.5319. Anal. Found: C, 62.61; H, 5.33. Calcd. for C17H17F3OS : C, 62.56; H, 5.25 %.

Workup

  1. temperatureAfter cooling
  2. extractionextracted twice benzene
  3. washThe combined organic layers were washed with 5 % sodium hydroxide solution, 5 % hydrochloric acid solution, and water
  4. dry with materialdried over sodium fulfate
  5. customThe solvent was removed
  6. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-2fb17c4858b6423396c573dcf64c8754
Source dataset
uspto-grants-1978_05
Patent number
US04091109

Reaction notes

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