Methanol → Methyl phenyl sulfoxide

Methyl phenyl sulphide (20 g, 161.03 mmol) was added to a mixture of methanol (100 ml) and water (20 mL). NBS (34.39 g, 1.2 eq) was added in portions maintaining the temperature between 0° and 5° C. The mixture was stirred at the same temperature until the reaction was complete. Thereafter, the reaction mixture was quenched by the addition of Na2SO3 (10%, 60 ml). The pH of the resulting 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. The residue was extracted with dichloromethane (2×125 mL). The combined organic layer was washed with water (2×125 mL) and concentrated to ⅓ of the volume. Heptane (20 mL) was added and then removed by distillation to give 21.64 g (95.9%) of the desired product as colourless oil.

1. temperaturemaintaining the temperature between 0° and 5° C
2. customThereafter, the reaction mixture was quenched by the addition of Na2SO3 (10%, 60 ml)
3. customThe pH of the resulting reaction mixture
4. concentrationThe mixture was concentrated under vacuum at a temperature between 20° C. and 25° C
5. extractionThe residue was extracted with dichloromethane (2×125 mL)
6. washThe combined organic layer was washed with water (2×125 mL)
7. concentrationconcentrated
8. additionHeptane (20 mL) was added
9. customremoved by distillation

ORD record

ord-8e32d617c813422ea108ba1b7aab2aa1

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09290446B2