Chlorosulfonic acid → 4-(3-Fluoropropyl)-benzenesulfonyl chloride

Temperature

2.5 °C

4.1 g of (3-fluoro-propyl)-benzene (29.67 mmol) were dissolved in 40 ml of dichloromethane. At 0-5° C., 6.91 g of chlorosulfonic acid (59.34 mmol), dissolved in 10 ml of dichloromethane, were added dropwise. The reaction mixture was stirred for 45 min at 0-5° C. and then added to a solution of 6.8 g of phosphorous pentachloride (32.63 mmol) dissolved in 50 ml of dichloromethane. The reaction mixture was stirred for 1 h at 5-10° C. The solvent was evaporated, 150 ml of diethyl ether added, washed once with 150 ml of ice water, and the organic layer dried over magnesium sulfate, filtered, and the solvent evaporated under reduced pressure. The crude product was purified via silica gel chromatography with n-heptane-dichloromethane (11:9) as eluent to give 5.5 g of the title compound.

1. additionwere added dropwise
2. stirringThe reaction mixture was stirred for 1 h at 5-10° C
3. customThe solvent was evaporated
4. addition150 ml of diethyl ether added
5. washwashed once with 150 ml of ice water
6. dry with materialthe organic layer dried over magnesium sulfate
7. filtrationfiltered
8. customthe solvent evaporated under reduced pressure
9. customThe crude product was purified via silica gel chromatography with n-heptane-dichloromethane (11:9) as eluent

ORD record

ord-0abebcda96f14e88b2c0f22e99ee2434

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08470810B2