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- Alc to Halide
- Alc to Cl
- Ex (cat. DMF)
Alcohol to Chloride
[SOCl2 + Solvent + DMF (cat.)]
Examples:
Example 1
To a solution of the SM (1.10 g, 3.37 mmol) and a catalytic amount of DMF (0.10 mL) in DCM (12.0 mL) at 0 C was slowly added SOCl2 (0.802 g, 6.74 mmol). The reaction mixture was stirred at RT for 1 h. The mixture was concentrated in vacuo and the resulting material was purified by silica gel column chromatography (eluting with 0-5% EtOAc/hexane) to provide the product. [1.15 g]
[Patent Reference: WO2010045258, page 119, 
(12.0 MB)]
Example 2
A mixture of the SM (200 mg, 1.4 mmol), DCM (4 mL), DMF (0.1 mL), and SOCl2 (1 mL) was stirred for 4 h. The pH was adjusted to about 7.0 with 4M aq NaHCO3 and extracted with DCM (3 x 50 mL). The combined organics were dried (Na2SO4) and concentrated to provide the product as an orange oil. [182 mg, 81%]
[Patent Referenc: WO2015069512, page 19, (2.6 MB)]