Acetaldehyde → Methyl 2-bromomethyl-2-butenoate

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.

1. extractionthe reaction mixture is extracted thrice with ether
2. washThe extract is washed with saturated saline
3. dry with materialdried over MgSO4
4. concentrationconcentrated
5. distillationThe resulting residue is distilled under reduced pressure

ORD record

ord-a4522165b2504ffd89b9ad41a58b80ee

Source dataset

uspto-grants-1990_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04960879