Synthesis
General procedure for the synthesis of 3-amino-3-(3-bromophenyl)propionic acid from m-bromobenzaldehyde and malonic acid: a mixture of 200 g (1.08 mol) of 3-bromobenzaldehyde, 112 g (1.08 mol) of malonic acid, and 166.5 g (2.16 mol) of ammonium acetate was suspended in 1.125 liters of anhydrous ethanol. The mixture was heated to reflux temperature under mechanical stirring until the solution became clear. The reflux reaction was maintained for 16 hours, during which time a precipitate was generated. Upon completion of the reaction, the mixture was cooled to 0 °C and the solid product was collected by filtration and washed with cold ethanol to yield 184 g (70% yield) of 3-amino-3-(3-bromophenyl)propionic acid as a white solid. The product was used directly in subsequent steps without further purification or analytical characterization.
References
[1] Advanced Synthesis and Catalysis, 2017, vol. 359, # 9, p. 1570 - 1576
[2] Patent: US2008/194535, 2008, A1. Location in patent: Page/Page column 25
[3] Journal of Organic Chemistry, 2009, vol. 74, # 23, p. 9152 - 9157
[4] Bulletin de la Societe Chimique de France, 1987, # 6, p. 1079 - 1083
[5] Chemistry - A European Journal, 2014, vol. 20, # 37, p. 11768 - 11775
