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

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.

1. extractionthe aqueous suspension was extracted with diethyl ether (3×15 mL)
2. extractionThe combined organic layers were back extracted with water (1×15 mL), saturated NaHCO3(aq.) (2×15 mL), and brine (1×15 mL)
3. dry with materialdried over MgSO4
4. filtrationfiltered
5. concentrationconcentrated in vacuo to 1.24 g (92%) of an oil
6. customThis was used in the next step on the same day and without further purification

ORD record

ord-ca6a85f36d424dc9a8a03184087f1f2f

Source dataset

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07888374B2