Ethanolamine → (RS)-1-(4-bromo-3-fluoro-phenyl)-2-(2-hydroxy-ethylamino)-ethanol

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Reaction Steps

2-(4-Bromo-3-fluoro-phenyl)-oxirane (25.1 g, 109 mmol) was combined with tetrahydrofurane (70 ml) to give a yellow solution. Ethanolamine (66.4 g, 65.1 ml, 1.09 mol) was added. The resulting orange solution was stirred at room temperature overnight. The reaction mixture was poured into brine and extracted twice with ethyl acetate. The organic layers were dried over MgSO4 and concentrated in vacuo to yield a yellow oil (27.9 g, 92%), MS (ISP): 277.9 ([{79Br}M+H]+), 279.9 ([{81Br}M+H]+).

Provenance & Evidence