反应详情

温度

100 °C

A mixture of methyl 2-cyclobutyl-5-iodo-4-methylbenzoate (219.3, 3.0 g, 9.1 mmol), Zn(CN)2 (2.3 g, 19.6 mmol) and Pd(PPh3)4 (0.55 g, 0.47 mmol) in DMF (50 ml) was degassed and the flask was filled with argon through a balloon. The mixture was heated at 100° C. under argon overnight. After cooling to ambient temperature, the reaction was quenched with saturated aq. FeSO4 (20 ml) and diluted with EtOAc (200 ml). The mixture was stirred vigorously then filtered through celite and washed with 1 M FeSO4, water and ethyl acetate. The layers were separated and the aqueous phase was extracted with ethyl acetate. The combined organic layers were washed with brine, dried (Na2SO4), and concentrated. The residue was purified using column (silica gel) chromatography (hexanes:EtOAc 30:1 to 20:1). Yield: 2.0 g, 96%. 1H NMR (400 MHz, Chloroform-d) δ 8.03 (s, 1H), 7.34 (s, 1H), 4.26-4.13 (m, 1H), 3.89 (s, 3H), 2.59 (s, 3H), 2.46-2.32 (m, 2H), 2.16-1.98 (m, 3H), 1.90-1.78 (m, 1H).

1. customwas degassed
2. additionthe flask was filled with argon through a balloon
3. temperatureAfter cooling to ambient temperature
4. customthe reaction was quenched with saturated aq. FeSO4 (20 ml)
5. additiondiluted with EtOAc (200 ml)
6. filtrationthen filtered through celite
7. washwashed with 1 M FeSO4, water and ethyl acetate
8. customThe layers were separated
9. extractionthe aqueous phase was extracted with ethyl acetate
10. washThe combined organic layers were washed with brine
11. dry with materialdried (Na2SO4)
12. concentrationconcentrated
13. customThe residue was purified