Hydrochloric Acid → tert-Butyl 2,4-dibromobutyrate

Participants

Reaction Steps

Bromine (31.3 ml, 0.54 mol) was added dropwise over 4 h at 100° C. to neat stirring 4-bromobutyryl chloride (100 g, 0.54 mol). The resulting acid chloride was cooled then added dropwise at 0° C. to a stirred solution of tert-butanol (240 ml) and triethylamine (64 ml, 0,461 mol) in anhydrous dichloromethane (600 ml). 2 M Hydrochloric acid was added and the layers separated. The organic portion was then washed sequentially with 10% sodium metabisulphite solution (2×500 ml), water (500 ml) and brine (500 ml), dried (MgSO4) and evaporated in vacuo to provide the title compound (120 g, 86%) as a brown liquid.

Provenance & Evidence