(R)-4-Chloro-3-hydroxybutyronitrile

(1) 19.19g (0.174mol) (R)-(-)-chloroglycerol, 50ml dichloromethane into a 250ml three-necked flask, under the condition of ice bath, 22.74g (0.191oml) dichlorosulfoxide was added slowly dropwise. React for 1h, add 40ml of water, the organic layer was washed twice with saturated saline, the aqueous layer was washed twice with ethyl acetate, the organic layers were combined and dried with anhydrous sodium sulfate. Filtration, filtrate concentrated under reduced pressure, obtained 27.23g colorless liquid. That is, cyclic sulfinic acid ester intermediate, without purification, directly used in the next step of the reaction, yield 100%.

(2) cast 10g (0.064mol) cyclic sulfinic acid ester, 30ml methanol to 100ml three-necked bottle, room temperature conditions, add 5.21g (0.08mol) KCN, stirring for 10min, and then raised to 50 , stirring vigorously for 12h. Concentrate under reduced pressure, add 15 ml of ethyl acetate and slowly add 20% H2SO4 solution dropwise. After stirring for 5h, add dilute NaCO3 solution washed twice, water washed twice, saturated brine washed once, the aqueous layer was washed with ethyl acetate, the organic layer was combined, and anhydrous sodium sulfate was added to dry. Decompression distillation was used to collect the 89-90C/<1 mmHg fraction, yielding 6.51 g of colorless liquid, i.e., chlorobutyronitrile intermediate, with a yield of 85%.