Iodine → 17-Bromoheptadecan-6-ol

Participants

Reaction Steps

1-bromopentane (2.54 ml, 20.51 mmol) in THF (5 ml) was added dropwise to a stirred suspension of Mg metal (0.54 g, 22.23 mmol) and a catalytic amount of iodine in dry THF (15 ml) at 75° C., after which stirring was continued for another 30 minutes. The generated Grignard reagent was cooled to room temperature and added slowly to a stirred solution of 12-bromododecanal (4.5 g, 17.09 mmol) in THF (40 ml) at 0° C. The reaction was warmed to room temperature and stirring continued another 1.5 hours, then quenched with NH4Cl solution, and extracted with EtOAc (3×50 ml). The combined organic layers were washed with brine solution, dried on MgSO4 and concentrated. The crude compound was purified over silica gel column (8% EtOAc in hexane) to give 17-bromoheptadecan-6-ol as an off-white low melting solid (3.34 g, 58%).

Provenance & Evidence