Sulfuric Acid → tert-Butyl 2-bromopropanoate

Participants

Reaction Conditions

Reaction Steps

Isobutylene (2.4 g, 42.8 mmoles) was condensed into a pressure bottle at −15° C. Dioxane (6 mL) and 2-bromopropionic acid (3.5 mL, 38.9 mmoles) were added and the mixture was stirred for 5 min, warmed to −10° C., and concentrated sulfuric acid (250 μL) was added. The bottle was scaled, the reaction mixture was stirred overnight at room temperature, and the bottle was then opened and the contents poured into dichloromethane (50 mL). The solution was washed with 2096 potassium carbonate (50 mL), water (50 ml), dried over anhydrous magnesium sulfate and evaporated to give t-butyl bromopropionate (2.17 g, 27%). 1HMR (CDCl3, δ): 4.31 (1H, q, 7.1 Hz), 1.81 (3H, d, 7.1 Hz), 1.52 (9H, s).

Provenance & Evidence