反应详情

温度

130 °C

To a round-bottom flask containing 3-iodo-4-methyl-benzoic acid methyl ester (1.38 g, 5.00 mmol), 4-cyanophenylboronic acid (1.10 g, 7.48 mmol), palladium acetate (168 mg, 0.748 mmol), 2-(dicyclohexylphosphino)biphenyl (0.526 g, 1.50 mmol) and potassium fluoride (0.870 g, 15.0 mmol) is added anhydrous 1,4-dioxane (15 ml). The flask is purged with argon and sealed. The mixture is stirred at 130° C. for 18 hours, cooled to ambient temperature and then water (20 ml) and ethyl acetate (20 ml) are added. Solid is removed under vacuum filtration. The filtrate is extracted with EtOAc (20 ml×2). The organic layers are combined, washed with aqueous HCl (5%, 20 ml) and saturated NaHCO3 (20 ml). It is dried over MgSO4, and concentrated. The residue is purified by silica gel column chromatography (EtOAc/Hexane, gradient) to give 4′-cyano-6-methyl-biphenyl-3-carboxylic acid methyl ester 2; LC-MS m/z: 252.1 (M+1).

1. customThe flask is purged with argon
2. customsealed
3. temperaturecooled to ambient temperature
4. additionwater (20 ml) and ethyl acetate (20 ml) are added
5. customSolid is removed under vacuum filtration
6. extractionThe filtrate is extracted with EtOAc (20 ml×2)
7. washwashed with aqueous HCl (5%, 20 ml) and saturated NaHCO3 (20 ml)
8. dry with materialIt is dried over MgSO4
9. concentrationconcentrated
10. customThe residue is purified by silica gel column chromatography (EtOAc/Hexane, gradient)