Hydrogen Bromide → (2R)-2-bromo-4-methylpentanoic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of D-leucine (50 g, 0.381 mol) in 570 mL of 3N HBr (aq) at 0° C. was added sodium nitrite (42 g, 1.6 eq) portion-wise over 1 hour and 15 minutes. The reaction was further stirred for 3 hrs at 0° C. then it was extracted with ether (1000 mL). After washing the ether layer with water (2×500 mL) it was dried over MgSO4 and concentrated. The red syrup was then co-evaporated with chloroform (3×200 mL) to remove the color and then it was pumped to give (2R)-2-bromo-4-methylpentanoic acid, as a colorless oil with a constant weight of 71.3 g.

Provenance & Evidence