反应详情

温度

100 °C

A mixture of methyl 4-cyclobutyl-5-iodo-2-methylbenzoate (compound 152.3, 4.17 g, 12.64 mmol), Zn(CN)2 (2.96 g, 25.21 mmol) and Pd(PPh3)4 (0.73 g, 0.63 mmol) in DMF (30 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 mixture was quenched with saturated aq. FeSO4 (20 ml) and diluted with EtOAc (200 ml). The greenish solid was removed by filtration through celite. The filtrate was partitioned between water and EtOAc. The EtOAc layer was washed with brine, dried (Na2SO4), and concentrated. The residue was purified using column (silica gel) chromatography (hexanes:EtOAc 30:1 to 20:1). Yield: 2.55 g, white solid, 88%. 1H NMR (400 MHz, Chloroform-d) δ 8.16 (s, 1H), 7.28 (s, 1H), 3.90 (s, 3H), 3.86-3.82 (m, 1H), 2.68 (s, 3H), 2.55-2.45 (m, 2H), 2.27-2.04 (m, 3H), 1.89-1.87 (m, 1H).

1. customwas degassed
2. additionthe flask was filled with argon through a balloon
3. temperatureAfter cooling to ambient temperature
4. customthe mixture was quenched with saturated aq. FeSO4 (20 ml)
5. additiondiluted with EtOAc (200 ml)
6. customThe greenish solid was removed by filtration through celite
7. customThe filtrate was partitioned between water and EtOAc
8. washThe EtOAc layer was washed with brine
9. dry with materialdried (Na2SO4)
10. concentrationconcentrated
11. customThe residue was purified