Sulfuric Acid → 3-(Benzyloxy)-2-bromopropanoic acid

Participants

Reaction Conditions

Reaction Steps

Racemic O-(phenylmethyl)serine (5 g, 25.6 mmol) and potassium bromide (10.7 g, 89.6 mmol) were dissolved in ice-cooled H2SO4 (2.5N) and treated with an solution of sodium nitrite (2.65 g) in water (30 ml) over 50 minutes (keeping the reaction temperature <4° C.). The reaction was then stirred at 0° C. for 45 minutes and then at rt for 1 h, extracted with ethyl acetate (3×100 ml). The combined organic extracts were washed with water, brine, dried (MgSO4), filtered and evaporated to give the product as a yellow oil (6 g, 90%).

Provenance & Evidence