Dimethyl Sulfate → Methyl 2-chloro-6-fluorobenzthioimidate

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Reaction Steps

Into a 25-mL three-necked round bottom flask equipped with a magnetic stirrer was added 2-chloro-6-fluorobenzthioamide (1.89 g, 10.0 mmol) and toluene (10 mL). Dimethylsulfate was added dropwise and the mixture was allowed to stir at reflux using a Dean Stark trap. The solids were removed via filtration and washed with small portions of toluene to give methyl 2-chloro-6-fluorobenzthioimidate as a light yellow solid: 2.7 g (87% yield): 1H NMR (DMSO-d6) δ7.7 (m, 1H), 7.5 (m, 2H), 3.3 (s, 3H), 2.7 (s, 3H); 98% pure by HPLC analysis.

Provenance & Evidence