Dimethyl Sulfoxide → 2-Chlorobenzyl azide

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Reaction Steps

Sodium azide (3.36 g, 51.1 mmol, Eq: 1.05) was charged in the reactor followed by DMSO (35.2 g, 32.0 ml) and Hunig's base (642 mg, 868 μl, 4.87 mmol, Eq: 0.1). The suspension was stirred for 10 Min. at 25° C. Then 1-chloro-2-(chloromethyl)benzene (8 g, 6.29 ml, 48.7 mmol, Eq: 1.00) was added dropwise over 60 min. (Tr=25° C.) and stirred at 25° C. until reaction completion (<2 h). The resulting white suspension was treated with water (1.6 g, 1.6 ml) and stirred for 45 Min. at R.T. The suspension was filtered and the filter cake was washed with DMSO (17.6 g, 16.0 ml) to give a colorless solution of 1-(azidomethyl)-2-chloro-benzene solution.

Provenance & Evidence