Methyl 2,3-dichloropropionate

Chemical Properties

clear colorless to slightly yellow liquid

Uses

Methyl 2,3-dichloropropionate can be used to produce 2-chloro-acrylic acid methyl ester at Heating. It is used as pharmaceutical intermediate.

Application

Methyl 2,3-Dichloropropanoate is a useful reagent in preparation of oxidative fragmentation and coupling of catharanthine analogs to vindoline.

Synthesis

Preparation of Methyl 2,3-dichloropropanoate:
Methyl acrylate (2366 g, 27.5 mol) and dimethylformamide (DMF) (40 g, 0.55 mol) was placed in a 3-liter three necked flask fitted with a stirrer, thermometer, inlet tube and gas trap. Chlorine (950 g, 0.48 mol) was passed into the methyl acrylate rapidly over a period of ten hours while the temperature was kept below 40°C. Reaction progress was monitored by gas chromatography (GC). When it seemed that 50 percent of chlorine was consumed, the reaction was stopped. The reaction mass was taken for distillation to separate methylacrylate and Methyl 2,3-dichloropropanoate. The contents were subjected to vacuum distillation. Methyl 2,3-dichloropropanoate was collected distilling at 70°C with 15mm.Yield (%):77.2, Purity (%) = 98.