反应详情

温度

35 °C

Add 1-iodo-4-nitrobenzene (100 g, 400 mmol), allyl alcohol (40 mL, 590 mmol), sodium bicarbonate (80 g, 940 mmol), palladium acetate (4.5 g, 0.05 mmol), tetra-N-butylammonium chloride (110 g, 390 mmol) and dimethylformamide (500 mL) to a 2 L flask and stir. Degas the reaction by pump purging with nitrogen, then heat to 35° C. for 30 hours. Cool the reaction to 0° C. and add methyl tert-butyl ether and water. Stir for 30 minutes then filter over Hyflo Super Cel®. Separate the layers and add tetrahydrofuran to the organic layer and wash with lithium chloride (5% aqueous) and brine. Dry the organic phase over MgSO4, filter over silica gel and concentrate under reduced pressure to give an oily residue. The title compound was used without purification. 1H NMR (CDCl3, 500.0 MHz): δ 9.81-9.85 (m, 1H), 8.10-8.18 (m, 2H), 7.34-7.40 (m, 2H), 3.00-3.10 (m, 2H), 2.80-3.10 (m, 2H).

1. customDegas
2. customthe reaction by pump
3. custompurging with nitrogen
4. temperatureCool
5. customthe reaction to 0° C.
6. stirringStir for 30 minutes
7. filtrationthen filter over Hyflo Super Cel®
8. customSeparate the layers
9. additionadd tetrahydrofuran to the organic layer
10. washwash with lithium chloride (5% aqueous) and brine
11. dry with materialDry the organic phase over MgSO4
12. filtrationfilter over silica gel
13. concentrationconcentrate under reduced pressure
14. customto give an oily residue
15. customThe title compound was used without purification