Dichloromethane → 2,5-Dichloro-4-methylthiophene-3-sulfonyl chloride

Temperature

10 °C

To a cooled (10° C.) solution of 3-methylthiophene (5 g, 50 mmol) in dichloromethane (15 mL) was added a solution of sulfuryl chloride (8.6 mL) in dichloromethane (5 mL). The reaction mixture was maintained at 10° C. for 30 minutes, then at ambient temperature for 16 hours. The reaction was concentrated and redissolved in dichloromethane (30 mL) and cooled to −10° C. To the cooled solution was added chlorosulfonic acid (2 mL, 100 mmol). The reaction was maintained at −10° C. for 30 minutes, then at ambient temperature for 16 hours, at which time it was poured into ice water (50 mL) and extracted with dichloromethane (50 mL). The organic layer was dried (Mg2SO4) and concentrated to furnish a brown oil (3.3 g, 25%).

1. concentrationThe reaction was concentrated
2. dissolutionredissolved in dichloromethane (30 mL)
3. temperaturecooled to −10° C
4. temperatureThe reaction was maintained at −10° C. for 30 minutes
5. waitat ambient temperature for 16 hours
6. extractionextracted with dichloromethane (50 mL)
7. dry with materialThe organic layer was dried (Mg2SO4)
8. concentrationconcentrated

ORD record

ord-d3a94c6cd2a949a99cb74eb9ff971a3b

Source dataset

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07091204B2