4-Toluenesulfonyl chloride → 2-Tosylthiophene

A mixture of p-toluenesulfonyl chloride (3 g, 15.7 mmol) and zinc chloride (3 g, 21.3 mmol) in acetonitrile (30 mL) was heated to reflux and thiophene (2.4 g, 28.5 mmol) was added dropwise. After refluxing for 4 h the mixture was cooled to rt and filtered through Celite. The filtrate was concentrated in vacuo and then 100 mL of sodium hydroxide (2 N) was added. The mixture was extracted with ethyl acetate (3×60 mL) and the combined organic layers were washed with hydrochloric acid (10%, 50 mL) and brine (100 mL), dried over anhydrous magnesium sulfate and filtered. The solvent was evaporated in vacuo and the product was purified by flash chromatography eluting with dichloromethane/hexane (2:3) to give the title compound (0.54 g, 15 mmol).

1. temperaturewas heated
2. temperatureto reflux
3. temperatureAfter refluxing for 4 h the mixture
4. filtrationfiltered through Celite
5. concentrationThe filtrate was concentrated in vacuo
6. addition100 mL of sodium hydroxide (2 N) was added
7. extractionThe mixture was extracted with ethyl acetate (3×60 mL)
8. washthe combined organic layers were washed with hydrochloric acid (10%, 50 mL) and brine (100 mL)
9. dry with materialdried over anhydrous magnesium sulfate
10. filtrationfiltered
11. customThe solvent was evaporated in vacuo
12. customthe product was purified by flash chromatography
13. washeluting with dichloromethane/hexane (2:3)

ORD record

ord-dcd43305a0ed45b6af4702663bdb4623

Source dataset

uspto-grants-2010_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07858785B2