Methanol → 1-(Fluoromethylsulfinyl)-4-methylbenzene

(Fluoromethyl)(p-tolyl)sulfane (52.09 g, 320.06 mmol) was added to a mixture of methanol (250 mL) and water (50 mL). The resulting mixture was cooled to a temperature between 0° C. and 5°. NBS (68.36 g, 1.2 eq) was added in small portions, maintaining the same temperature range. The reaction mixture was stirred at the same temperature range until the reaction was complete. After that, the reaction mixture was quenched by the addition of Na2SO3 (10%, 150 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. The residue was extracted with dichloromethane (200 mL, 150 mL). The combined organic layer was washed with water (2×300 ml) and concentrated to 1/3 of the volume. Heptane (50 mL) was added and then removed by distillation. The crude product was purified by flash chromatography (Ethyl Acetate/Hexane 30:70) to give 48.32 g (88%) of the desired product as a white solid.

1. temperatureThe resulting mixture was cooled to a temperature between 0° C. and 5°
2. temperaturemaintaining the same temperature range
3. customAfter that, the reaction mixture was quenched by the addition of Na2SO3 (10%, 150 mL)
4. concentrationThe mixture was concentrated under vacuum at a temperature between 20° C. and 25° C
5. extractionThe residue was extracted with dichloromethane (200 mL, 150 mL)
6. washThe combined organic layer was washed with water (2×300 ml)
7. concentrationconcentrated to 1/3 of the volume
8. additionHeptane (50 mL) was added
9. customremoved by distillation
10. customThe crude product was purified by flash chromatography (Ethyl Acetate/Hexane 30:70)

ORD record

ord-da08cb3085bc42588e96a43d85d0fd58

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09359294B2