1-Bromopentane → HCID 21472391, compound

Participants

Reaction Steps

A mixture of 4-iodophenol (6.6 g), 1-bromopentane (4.5 g), anhydrous potassium carbonate (13.8 g) and acetone (100 ml) was stirred at reflux for 24 hours, with the additions of a further quantity of 1-bromopentane after 4 hours (4.5 g) and 8 hours (4.5 g). The acetone was removed by evaporation. The residue was triturated with water (50 ml) and extracted with ether (3×30 ml). The organic extracts were combined, dried (MgSO4) and evaporated. The residue, a colourless oil, was distilled at 160° C. and 0.05 mm pressure (using a Kugelrohr oven) to give 4-n-pentyloxyiodobenzene as a colourless oil (7.8 g); microanalysis, found C, 45.7; H, 5.4%; C11H15IO requires: C, 45.5; H, 5.2%; NMR(DMSO-d6): 0.84-0.95(3H,t), 1.25-1.48(4H,m), 1.62-1.77(2H,m), 3.88-3.97(2H,t), 6.72-6.8(2H,d), 7.52-7.6(2H,d); m/z 290 (M).

Provenance & Evidence