DL-leucine → 2-Bromo-4-methylpentanoic acid

Participants

Reaction Steps

D,L-Leucine (50 g, 0.38 mol) and potassium bromide (158.7 g, 1.33 mol) were dissolved in aqueous sulfuric acid (from 75 mL of H2SO4 and 250 mL of water), and sodium nitrite (34.8 g, 0.5 mol) was added portionwise wile keeping the temperature below −1° C. The mixture was kept at 0° C. for 1 h, then dichloromethane was added under stirring. The dichlomethane layer was collected and the aqueous phase was extracted twice with further portions of dichloromethane. The combined dichloromethane extracts were dried (Na2SO4) and evaporated to give the title compound as a pale yellow oil (63.4 g, 0.32 mol; 85.5%).

Provenance & Evidence