Thionyl Chloride → 2-Bromo-5-(chloromethyl)pyridine

Temperature

-60 °C

3.69 g (19.7 mmol) of the compound from Example 4A are initially introduced into the reaction vessel under argon and 25 ml thionyl chloride are added dropwise at −60° C. (bath temperature). The mixture is stirred at −60° C. for 1 h. It is concentrated at RT on a rotary evaporator, and 50 ml saturated sodium bicarbonate solution and 50 ml ethyl acetate are added to the residue. The aqueous phase is extracted with ethyl acetate (four times with 25 ml each time). The combined organic phases are dried over sodium sulfate and filtered, the solvent is removed on a rotary evaporator and the residue is dried in vacuo.

1. concentrationIt is concentrated at RT on a rotary evaporator, and 50 ml saturated sodium bicarbonate solution and 50 ml ethyl acetate
2. additionare added to the residue
3. extractionThe aqueous phase is extracted with ethyl acetate (four times with 25 ml each time)
4. dry with materialThe combined organic phases are dried over sodium sulfate
5. filtrationfiltered
6. customthe solvent is removed on a rotary evaporator
7. customthe residue is dried in vacuo

ORD record

ord-1649e40ab6244c02a442e2e7d6d94cff

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08252817B2