Azobisisobutyronitrile → 4-(Bromomethyl)-5-methyl-1,3-dioxol-2-one

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Reaction Steps

In 150 ml of carbon tetrachloride was dissolved 3.42 g of 4,5-dimethyl-1,3-dioxolen-2-one (synthesized by the method described in Tetrahedron Letters, 1972 pages 1701-1704). N-bromosuccinimide (5.34 g) and a catalytic amount of α,α'-azobisisobutyronitrile were added to the solution, and the mixture was heated under reflux for 15 minutes. The reaction mixture was concentrated to one half of its volume, and the insoluble material was removed by filtration. The filtrate was concentrated, and the syrupy residue was distilled under reduced pressure to give 4.2 g (yield 73%) of a colorless liquid having a boiling point of 115°-120° C./5 mm. The product had the following properties.

Provenance & Evidence