反应详情

温度

100 °C

To a solution of tert-butyl 5-bromo-2-chlorophenylcarbamate (1) (1.0 equiv.) in acetonitrile (0.3M) and EtOH (0.5M) was added K2CO3 (2.0 equiv.). The reaction was degassed and flushed with N2, then added (E)-ethyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)acrylate (2) (1.2 equiv.) and Pd(PPh3)4 (0.1 equiv.). The reaction was flushed again with N2 and stirred at 100° C. overnight. After cooling to room temperature, hexane was added, and the mixture was filtered through a pad of silica, eluting with EA/Hex (1:1) until the product was completely eluted. The filtrate was concentrated and purified on Combiflash, eluting with 0-15% EA in Hex to give (E)-ethyl 3-(3-(tert-butoxycarbonylamino)-4-chlorophenyl)acrylate (3) as a white solid.

1. customThe reaction was degassed
2. customflushed with N2
3. customThe reaction was flushed again with N2
4. temperatureAfter cooling to room temperature
5. additionhexane was added
6. filtrationthe mixture was filtered through a pad of silica
7. washeluting with EA/Hex (1:1) until the product
8. washwas completely eluted
9. concentrationThe filtrate was concentrated
10. custompurified on Combiflash
11. washeluting with 0-15% EA in Hex