Water → 4-bromo-3-methyl-N-trimethylsilanylmethyl-thiobenzimidic acid methyl ester

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Reaction Steps

To a solution of 4-bromo-3-methyl-N-trimethylsilanylmethyl-thiobenzamide (5.00 g, 15.8 mmol) in THF (30 mL) was added methyl iodide (1.97 mL, 4.49 g, 31.6 mmol) and Cs2CO3 (10.3 g, 31.6 mmol) at −5° C. After 1 h at this temperature, the mixture was allowed to reach room temperature and stirred over night. Water was added and the mixture was extracted three times with MTBE. The combined organic phases were dried over Na2SO4, filtered and concentrated in vacuum. The residue was purified by filtration over a short plug of silica gel to give the title compound (4.4 g), which was used in the next step without further purification.

Provenance & Evidence