Methanol → 1-[(Chloromethyl)sulfinyl]-4-methylbenzene

(Choromethyl)(p-tolyl)sulfane (10 g, 57.91 mmol) was added to a mixture of methanol (50 mL) and water (10 mL). The resulting mixture was cooled to a temperature between 0° C. and 5° C. NBS (12.37 g, 1.2 eq) was added in small portions, maintaining the same temperature range. The reaction mixture was stirred within the same temperature range until the reaction was complete. Thereafter, the reaction mixture was quenched by the addition of Na2SO3 (10%, 30 mL). The pH of the reaction mixture was adjusted to a value between 7 and 8, with saturated NaHCO3 solution. The mixture was concentrated under vacuum at a temperature between 20° C. and 25° C. and then extracted with dichloromethane (40 mL, 30 mL). The combined organic layer was washed with water (2×60 ml) and concentrated to 1/3 of the volume. Heptane (10 mL) was added and then removed by distillation. The crude product was purified by flash chromatography (Ethyl Acetate/Hexane 30:70) to give 9.78 g (89.51%) of the desired product as a white solid.

1. temperatureThe resulting mixture was cooled to a temperature between 0° C. and 5° C
2. temperaturemaintaining the same temperature range
3. customThereafter, the reaction mixture was quenched by the addition of Na2SO3 (10%, 30 mL)
4. concentrationThe mixture was concentrated under vacuum at a temperature between 20° C. and 25° C.
5. extractionextracted with dichloromethane (40 mL, 30 mL)
6. washThe combined organic layer was washed with water (2×60 ml)
7. concentrationconcentrated to 1/3 of the volume
8. additionHeptane (10 mL) was added
9. customremoved by distillation
10. customThe crude product was purified by flash chromatography (Ethyl Acetate/Hexane 30:70)

ORD record

ord-8a853981ef43482a96230bd9d6ee3768

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09359294B2