反应详情

温度

140 °C

Palladium acetate (169 mg, 0.75 mmol) and triphenylphosphine (420 mg, 1.6 mmol) were added to a solution of ethenesulfonic acid (1,1,3,3-tetramethyl-butyl)-amide (10 g, 45.7 mmol) and 2-bromo-thiophene (3.74 mL, 39.1 mmol) in N,N-dimethylformamide (75 mL). Triethylamine (14.7 mL, 105.5 mmol) was added and the mixture was flushed with nitrogen and heated at 140° C. for 16 hours. The mixture was cooled to room temperature and 1N HCl (250 mL) was added in one portion. The mixture was extracted with ethyl acetate (3×200 mL) and the combined organics were dried over MgSO4, filtered and concentrated in vacuo to afford a solid. The solid was purified by dry flash chromatography (SiO2, heptane to 1:1 heptane: ethyl acetate). The fractions were combined to afford (E)-2-thiophen-2-yl-ethenesulfonic acid (1,1,3,3-tetramethyl-butyl)-amide (2.5g, 21% yield).

1. customthe mixture was flushed with nitrogen
2. temperatureThe mixture was cooled to room temperature
3. addition1N HCl (250 mL) was added in one portion
4. extractionThe mixture was extracted with ethyl acetate (3×200 mL)
5. dry with materialthe combined organics were dried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customto afford a solid
9. customThe solid was purified
10. dry with materialby dry flash chromatography (SiO2, heptane to 1:1 heptane: ethyl acetate)