D-Phenylalanine → 3-(2-Bromophenyl)propionic acid

Participants

Reaction Conditions

Reaction Steps

Sodium nitrite (10.3 g, 280 mmol) was added to a solution of D-phenylalanine (30.0 g, 181 mmol) and potassium bromide (73.5 g) in sulfuric acid (2.5N, 365 ml) over a period of one hour while maintaining the temperature of the reaction mixture at 0° C. The mixture was stirred for an additional hour at 0° C. and then for one hour at room temperature. The reaction solution was extracted with ether, the ether was back extracted with water, and the ether layer was dried over sodium sulfate. Ether was removed in vacuo, and distillation of the oily residue afforded 25.7 g of (R)-2-bromo-3-benzenepropanoic acid; b.p. 141° C. (0.55 mm of Hg); [α]D =+14.5° (c=2.4, chloroform).

Provenance & Evidence