N-bromobutanimide → Chloromethyl phenyl sulfoxide

Chloromethyl phenyl sulfide (3 g, 18.9 mmol) was dissolved in a mixture of methanol (15 mL) and water (3 mL) The resulting mixture was cooled to a temperature between 0° C. and 5° C. NBS (4.04 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 solution (10%, 15 mL). The pH of the reaction mixture was adjusted to a value between 7 and 8, with saturated NaHCO3 solution. The resulting mixture was extracted with dichloromethane (3×50 mL). The combined organic layer was dried with anhydrous MgSO4 and concentrated. The crude product was purified by medium pressure chromatography (Ethyl Acetate/Hexane 2:8) to give 1.381 g (42%) of the desired product as a colourless liquid. 1H NMR (CDCl3, 400 MHz): δ 7.71-7.69 (2H, m), 7.57-7.56 (3H, m), 4.41 (2H, ABQ, J=10.8 Hz). 13C NMR (CDCl3, 100 MHz): δ 140.8, 132.1, 126.3, 124.8, 61.3. FT-IR (NaCl): 3058, 3004, 2935, 1472, 1444, 1384, 1218, 1085, 1052 cm−1.

1. temperaturewas 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 solution (10%, 15 mL)
4. extractionThe resulting mixture was extracted with dichloromethane (3×50 mL)
5. dry with materialThe combined organic layer was dried with anhydrous MgSO4
6. concentrationconcentrated
7. customThe crude product was purified by medium pressure chromatography (Ethyl Acetate/Hexane 2:8)

ORD record

ord-1b6c3cfac4084a8ea8124d824902ee52

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09359294B2