Thionyl Chloride → 4-(Chloromethyl)-2-methoxypyridine

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Reaction Steps

1.57 ml (21.6 mmol) of SOCl2 are added dropwise, whilst cooling with ice and under a N2 atmosphere, to a solution of 1.5 g (10.8 mmol) of 2-methoxy-4-(hydroxymethyl)-pyridine [for preparation see J. Org. Chem. 54 (1989), 5580] in 13 ml of chloroform. After 16 h at RT, the mixture is concentrated by evaporation, water and 2N sodium hydroxide solution are added to the residue, and extraction immediately takes place 3 times with chloroform. The organic phases are washed with water and brine, dried (Na2SO4) and concentrated by evaporation to form 2-methoxy-pyridin-4-yl-methylchloride; 1H NMR (CDCl3) δ8.15 (d, 1H), 6.90 (d, 1H), 6.76 (s, 1H), 4.49 (s, 2H), 3.94 (s, H3C).

Provenance & Evidence