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  (Organic Chemistry)

Alcohol to Chloride

(SOCl2 + Solvent)


Example 1

To a solution of the SM (460 mg, 2.13 mmol) in DCM (30 mL) was added SOCl2 (1.55 mL, 21.3 mmol). The mixture was stirred at RT for 2 h, after which time it was concentrated in vacuo. The residue was dissolved in DCM and concentrated twice to help remove any remaining SOCl2 and provide the HCl salt of the product as a yellow solid. [520 mg, 90 %]

[Patent Reference: WO2012112946, page 111, (11.2 MB)]

Example 2

To a mixture of the SM (174 mg, 0.878 mmol) and dry DCM (10 mL) in a 20 mL microwave vial was slowly added SOCl2 (1.0 mL, 13.78 mmol). The mixture was irradiated at 80 C in a microwave reactor for 20 min. The resulting mixture was concentrated in vacuo. The residue was taken up in DCM (20 mL) and concentrated in vacuo (repeated 3x) to provide the product as a grey solid. [189 mg, 99%]

[Patent Reference: WO2012112946, page 51, (11.2 MB)]

Example 3

To a solution of the SM (294 g, 1.90 mol) in DCM (2.2 L) at -10 C  was added SOCl2 (460 g, 3.90 mmol). The reaction mixture was stirred at reflux for 1 h. The mixture was concentrated in vacuo to provide crude product which was taken directly to the next step. [298 g, 92%]

[Patent Reference: WO2016014463, page 91, (6.7 MB)]