Triphenylphosphine → Phosphonium, [(4-methoxy-3-nitrophenyl)methyl]triphenyl-, bromide

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Reaction Conditions

Reaction Steps

3-Nitro-4-methoxybenzyl bromide (3, 119 g) is charged into 1000 ml of stirred toluene in a 2 litre three-necked flask equipped with a mechanical stirrer, a thermometer, a T piece, a funnel for the addition of solids and a reflux condenser surmounted by a bubble counter, and the stirred mixture, warmed to 25° C., forms a solution. Triphenylphosphine (126.5 g) is then added and the resultant solution is gradually heated to 60° C.; a precipitate begins to form at about 30° C. The mixture is maintained at 60-65° C. for 4 hours, is then cooled to 30° C. and is filtered through a sintered glass filter. The filter cake is washed on the filter twice with 300 ml portions of toluene, sucked dry and dried in an oven (35° C./20 mmHg/ hours). (4-Methoxy-3-nitrobenzyl)triphenylphosphonium bromide (217 g) is obtained with a chemical yield of 88%. The synthesis is also described in the publication: (solvent used: dichloromethane) K. G. Piney et al., Bioorg. Med. Chem., 8(2000), 2417-2425.

Provenance & Evidence