3-Chlorobenzenesulphonyl chloride → Sodium 3-chlorobenzene-1-sulfinate

A solution of sodium sulphite (627 mg, 4.98 mmol) and sodium bicarbonate (418 mg, 4.98 mmol) in water (13 mL) was stirred vigorously with 3-chlorobenzenesulfonyl chloride (500 mg, 2.36 mmol) at 0° C. for 30 min then heated at 65° C. for 3 h. After cooling to ambient temperature, the reaction mixture was washed with dichloromethane (2×20 mL) and lyophilized. The resulting white solid was stirred with methanol (10 mL) for 5 min and the insoluble inorganic salts removed by filtration. The filtrate was concentrated in vacuo to approximately 3 mL and an equal volume of diethyl ether added. The precipitated solid containing residual inorganic salts was filtered and set aside. The remaining filtrate was diluted with excess diethyl ether, filtered and the filtered solid dried in vacuo to give sodium 3-chloro-benzenesulfinate (306 mg, 65%) as a white solid: 1H NMR (DMSO-d6, 300 MHz) δ 7.43 (br s, 1H), 7.35-7.39 (m, 1H), 7.32 (d, J=7.2 Hz, 1H), 7.26 (dt, J=7.5, 1.8 Hz, 1H).

1. temperatureAfter cooling to ambient temperature
2. washthe reaction mixture was washed with dichloromethane (2×20 mL)
3. customthe insoluble inorganic salts removed by filtration
4. concentrationThe filtrate was concentrated in vacuo to approximately 3 mL
5. additionan equal volume of diethyl ether added
6. additionThe precipitated solid containing residual inorganic salts
7. filtrationwas filtered
8. additionThe remaining filtrate was diluted with excess diethyl ether
9. filtrationfiltered
10. customthe filtered solid dried in vacuo

ORD-Eintrag

ord-951d8adc01644c28ae1ea18cb1fe87aa

Quelldatensatz

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09067949B2