Preparation
2-Bromothiazole (5.0 g, 30.5 mmol) was added stepwise to n-BuLi (14.6 mL of 1.6 M hexane, 36.6 mmol) in Et₂O (60 mL) at -78°C under nitrogen. The reaction mixture was stirred for 40 minutes, then dimethyl sulfate (4.75 mL, 50.3 mmol) was added dropwise, and the reaction mixture was heated to -10°C (and placed in a refrigerator) and allowed to stand overnight. The reaction mixture was heated to 0°C and carefully quenched with 2 M HCl (40 mL). The organic layer was separated and extracted with 2 M HCl (2×). The acidic extract was combined with 2 M NaOH to form a strongly basic solution and extracted with Et₂O (4×). The combined organic extract was dried over KOH, the solvent was distilled at atmospheric pressure, and then 2-methylthiazole was distilled off at 128–130°C.
