1,2-Dibromoethane → 1-(2-Bromoethoxy)-2,4-dichlorobenzene

Participants

Reaction Steps

A mixture of 160.0 g (1.0 mole) 2,4-dichlorophenol, 235.0 g (1.26 mole) 1,2-dibromoethane, and 500 ml water were heated at reflux, during which time a solution of 42 g (1.05 mole) sodium hydroxide in 125 ml water was added to the mixture over a period of one hour. The solution was allowed to reflux for 10 hours, cooled and the organic layer distilled to give 176.0 g of 1-bromo-2-(2,4-dichlorophenoxy)ethane (b.p. 157°-160° C at 10 mm). A 15.0 g (0.055 mole) portion of this material was dissolved in 200 ml toluene and to this solution was added 7.8 g (0.055 mole) hexamethylene tetramine. The mixture was allowed to reflux for 24 hours. The precipitate was filtered, further purified by washing with ether, and air dried to give 18.1 g of a white powder identified as 3,5,7-triaza-1-azoniatricyclo(3.3.1.13,7)decane:1-(2-(2,4-dichlorophenoxy)ethyl)-, bromide (hereinafter referred to as Compound 1) m.p. 165°-169° C. The yield was calculated to be 79% from the phenoxyethyl bromide.

Provenance & Evidence