off-white to brown crystalline powder
3-Bromo-2-(bromomethyl)propionic acid acts as an organic building block for the preparation of beta-substituted acrylates. It is used in the preparation of t-butyl 2-(phenylthiomethyl) propenoate, t-butyl 3-(phenylthio)-2-(phenylthiomethyl)propenoate and 3-(phenylthio)-2-(phenyl-sulfinylmethyl)propenoate. Further, it plays an important role in the synthesis of beta-lactams by cyclization of the corresponding amide.
3-Bromo-2-(bromomethyl)propionic acid reacts with alkaline arsenite to yield (RS)-3-arsono-2-(hydroxymethyl)propionic acid.
A mixture of commercially available diethyl bis(hydroxymethyl)malonate (25 g., 0.11 mol.) and a 48%
aqueous hydrogen bromide solution (192 cm3, 1.70 mol) was heated until the ethyl bromide liquid began to evaporate from the mixture and then vigorously distilled for about 1 h.
The reaction mixture was refluxed at 140C for 5 hours. The solution is cooled in an ice bath for 1. 5 hours. The crystals formed were filtered, washed with a small amount of ice-cold water and dried under vacuum. About 80 cm3 was distilled out of the
of the filtrate, the solution was cooled in ice to produce another batch of crystals, washed and dried as before to give 3-bromo-2-bromomethylpropionic acid.
