Furan → Furan-2-sulfonyl Chloride

Temperature

0 °C

Phosphorus pentachloride (15.29 g, 73.44 mmol) was added portionwise (caution, foaming) over 5 min at 0° C. to chlorosulfonic acid (21.39 g, 183.6 mmol) and the resulting solution was stirred at 0° C. for 10 min. Then, furan (5.0 g, 73.44 mmol) was added in one portion and the resulting dark suspension was stirred at 0° C. for 15 min during which time foaming occurred and subsided. The reaction mixture was then poured onto ice and the resulting suspension was extracted with CH2Cl2 (150 mL). The organic extract was filtered through a pad of celite, washed with brine and dried over MgSO4. The solvent was removed in vacuo to provide 2-furansulfonyl chloride as a black oil (1.01 g, 7.9%). 1H-NMR (DMSO-d6, 400 MHz) δ7.4 (d, 1H); 6.38 (d, 1H); 6.35 (d, 1H).

1. stirringthe resulting dark suspension was stirred at 0° C. for 15 min during which time
2. additionThe reaction mixture was then poured onto ice
3. extractionthe resulting suspension was extracted with CH2Cl2 (150 mL)
4. extractionThe organic extract
5. filtrationwas filtered through a pad of celite
6. washwashed with brine
7. dry with materialdried over MgSO4
8. customThe solvent was removed in vacuo

ORD record

ord-803c3cf65af6429dbfaf1754a5f882ad

Source dataset

uspto-grants-2003_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06610734B2