2-(Dimethylamino)ethanol → [2-(3-Bromophenoxy)ethyl]dimethylamine

Participants

Reaction Steps

Diisopropyl diazene-1,2-dicarboxylate (1.56 g, 7.34 mmol) was added dropwise to a 0° C. solution of 3-bromophenol (1.155 g, 6.68 mmol), 2-(dimethylamino)ethanol (0.65 g, 7.34 mmol) and triphenylphosphine (1.93 g, 7.34 mmol) in THF (20 mL). The mixture was allowed to warm to room temperature over 16 hours, and then the volatiles were removed under reduced pressure. The resulting residue was partitioned between ethyl acetate (20 mL) and 1N HCl (20 mL), and the aqueous layer was collected and washed with ethyl acetate. The aqueous layer was neutralized with saturated NaHCO3 (50 mL), extracted with ethyl acetate, and dried (MgSO4). Purification via silica chromatography (eluting with 4% MeOH/DCM) afforded 2-(3-bromophenoxy)-N,N-dimethylethanamine (1.03 g, 63%) as an oil.

Provenance & Evidence