Carbon tetrabromide → 3-(3-Bromopropyl)oxolane

Participants

Reaction Conditions

Reaction Steps

3-(Tetrahydro-3-furanyl)-1-propanol (1 g, 7.68 mmol) was dissolved in DMF (10 ml) and carbon tetrabromide (5.09 g, 15.36 mmol) added. The solution turned yellow. The solution was cooled to 0° C. and triphenylphosphine (4.03 g, 15.36 mmol) added dropwise as a solution in DMF (20 ml) (˜30 mins, temperature maintained <2° C. throughout). The reaction mixture was stirred at 0° C. for 1 hour before gradually allowing to warm to room temperature and stirred for a further 2 hours. The solvent was removed in vacuo. Attempted trituration of the resultant brown oil with either DCM or cyclohexane was unsuccessful. The solvent was removed and the oil diluted with DCM and was purified by chromatography on silica (100 g) using a 0-25% ethyl acetate-cyclohexane over 40 mins using a Flashmaster II. The appropriate fractions were combined and dried down to give the title compound as a yellow oil (0.676 g).

Provenance & Evidence