1,5-Dibromopentane → HCID 131716418, compound

Participants

Reaction Steps

A mixture of 36.5 g of 4-methyl-3-n-propylthiophenol, 11.5 g of 1,5-dibromopentane, 80 ml of water, 0.5 g of tetrabutylammonium bromide and 10 ml of toluene was stirred drastically and heated at 80° to 90° C. At this temperature, a solution of 8.6 g of sodium hydroxide and 20 ml of water was added dropwise to the mixture during 1 hour. The reaction was finished by stirring for 2 hours after the dropwise addition. After cooling, the reaction mixture was added with 150 ml of toluene, and separated to layers. A toluene layer was washed with water, and dried over anhydrous sodium sulfate. Then, the residue obtained by distilling off toluene and an excess of 1,5-dibromopentane under reduced pressure, was purified by silica-gel column chromatography (developing solvents: toluene+n-hexane) to give 45.9 g of the intended 1-bromo-5-(4-methyl-3-n-propylthiophenoxy)-n-pentane (yield: 69.3%) as a colorless oil. nD25 1.5569.

Provenance & Evidence