反应详情

温度

120 °C

To a solution of methyl 3-bromo-2-methylbenzoate (0.646 g, 2.8 mmol) in 4 ml of dimethylamine was added Pd(OAc)2 (0.5 mol %), sodium carbonate (0.3 g, 2.8 mmol), K4[Fe(CN)6].3H2O (0.262 g, 0.62 mmol). The mixture was heated to 120° C. and stirred at this temperature for 4 hours then at RT for 18 hours. The reaction mixture was diluted with 30 ml of ethyl acetate and the resulting slurry was filtered through Celite. The filtrate was washed with water (2×15 ml) then 5% aqueous ammonium hydroxide (1×15 ml). The organic layer was dried over anhydrous sodium sulfate then filtered and concentrated to provide methyl 3-cyano-2-methylbenzoate (0.248 g, 50% yield) (S. Weissman, D. Zewge, C. Chen, J. Org. Chem. 2005, 70, 1508-1510). 1H-NMR (400 MHz, DMSO-d6): 8.09 (d, 1H), 8.04 (d, 1H), 7.53 (t, 1H), 3.87 (s, 3H), 2.66 (s, 3H).

1. waitat RT for 18 hours
2. filtrationthe resulting slurry was filtered through Celite
3. washThe filtrate was washed with water (2×15 ml)
4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
5. filtrationthen filtered
6. concentrationconcentrated