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

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 %.

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

ORD-Eintrag

ord-2fb17c4858b6423396c573dcf64c8754

Quelldatensatz

uspto-grants-1978_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US04091109