Acetaldehyde → Methyl 2-bromomethyl-2-butenoate

Participants

Reaction Steps

In a manner to that of S. E. Drews, D. Emsley, et al., in J. Chem. Soc., Perkin Transaction I, pp. 2079 and 2079 (1982), an ice cooled solution of methyl acrylate (IV) (8.6 g) in conc. HBr (16.5 ml) is mixed dropwise with acetaldehyde (V) (4.4 g) and then conc. sulfuric acid (15 ml). After stirring overnight, the reaction mixture is extracted thrice with ether. The extract is washed with saturated saline, dried over MgSO4, and concentrated. The resulting residue is distilled under reduced pressure to give methyl 2-bromomethyl-2-butenoate (III) (8.59 g). 83°~85° C./10 mmHg.

Provenance & Evidence