Sodium Iodide → Hydroxybupropion

Participants

Reaction Steps

2-Amino-1-methyl-propan-1-ol (14 ml, 0.15 mol) was added to α-bromo-3′chloro propiophenone (18 g, 73 mmol) in suspension in chloroform (50 ml), with two crystals of sodium iodide. The reaction was heated under reflux overnight. After filtration the organic phase was extracted twice with a 2M HCl solution (2×100 ml). The aqueous phase wash washed with DCM then neutralised with sodium carbonate. The aqueous layer was extracted with DCM. The organic phase was dried over magnesium sulphate, filtered and evaporated. Recrystallisation from chloroform gives the desired compound in 55% yield as a white solid (10.2 g, 40 mmol).

Provenance & Evidence