Water → 2-Chloromethyl-1-methoxy-4-methylsulfanyl-benzene

Participants

Reaction Steps

To a solution of Example 170B (1.23 g, 6.69 mmol) in 15 mL of N,N-dimethylformamide was added LiCl (567 mg, 13.4 mmol), then 2 mL (27 mmol) of thionyl chloride. The solution warmed spontaneously on addition of the thionyl chloride. After 15 min, 50 mL of water was added, then the aqueous suspension was extracted with diethyl ether (3×15 mL). The combined organic layers were back extracted with water (1×15 mL), saturated NaHCO3(aq.) (2×15 mL), and brine (1×15 mL), dried over MgSO4, filtered, and concentrated in vacuo to 1.24 g (92%) of an oil. This was used in the next step on the same day and without further purification.

Provenance & Evidence