Pyridine → 1-(4-Bromobutoxy)-3-methylbutane

Participants

Reaction Steps

6.1 cc (0.0636 mol) of phosphoric tribromide are added dropwise at 0° over the course of 20 minutes and while stirring, to a solution of 27.5 g (0.172 mol) of 4-isopentyloxy-butanol (production: see Example 15) and 1.36 g (0.0172 mol) of pyridine in 150 cc of absolute chloroform. The cooling bath is removed, the mixture is then heated to 60° for 1 hour and stirred at this temperature for 18 hours. The reaction mixture is poured into ice-cold sodium bicarbonate solution, the chloroform phase is removed in a separating funnel, washed with water and saturated sodium chloride solution, dried over magnesium sulphate and evaporated. The residue is filtered with hexane/ethyl acetate (98:2) on silica gel. The evaporated filtrate is fractionally distilled and pure 1-bromo-4-isopentyloxy-butane is obtained. B.P.: 96°-97°/12 mm Hg.

Provenance & Evidence