Thionyl Chloride → 2-Chloromethyl-3,4-dimethoxypyridinium chloride

Participants

Reaction Steps

A solution of (3,4-dimethoxypyridin-2-yl)methanol (1 g, 5.91 mmol) in CH2CH2 (11.82 mL) was treated dropwise with thionyl chloride (1 mL, 13.70 mmol) with stirring at room temperature. The reaction mixture was stirred for 2 h, and then concentrated directly in vacuo. The resulting residue was washed with 3×10 mL Et2O, the resulting solids collected by filtration, and then dried under reduced pressure to afford the title compound as a white solid (1.12 g, 85%), which was used in the subsequent step without further purification. Data for 1-1: LC/MS: rt=0.58 min, m/z (M+H)=188.09 found; 188.04 required. 3,4-dimethoxy-2-{[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]methyl}-pyridine (1-2)

Provenance & Evidence