反应详情

To a solution of 5.0 g (0.021 mol) of 2-amino-5-bromo-3-methyl-benzoic acid methyl ester and 2.8 g (0.023 mol) of phenyl boronic acid in 150 mL of dimethoxyethane was added 20.5 mL of a 2.0M aqueous solution of Na2CO3 and 1.18 g (1.02 mmol) of Pd(PPh3)4. The reaction mixture was evacuated and filled with N2 three times and was then heated to reflux overnight. The reaction was then cooled to room temperature, and poured into ethyl acetate and water. The aqueous layer was extracted three times with ethyl acetate. The combined organics were washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was chromatographed on silica gel using gradient elution (100% hexane to 4/1 hexane/ethyl acetate) to provide 2.5 g (50%) of 4-amino-5-methyl-biphenyl-3-carboxylic acid methyl ester. Electrospray Mass Spec: 241.8 (M+H)+

1. customThe reaction mixture was evacuated
2. additionfilled with N2 three times
3. temperaturewas then heated
4. temperatureto reflux overnight
5. additionpoured into ethyl acetate and water
6. extractionThe aqueous layer was extracted three times with ethyl acetate
7. washThe combined organics were washed with brine
8. dry with materialdried over MgSO4
9. concentrationconcentrated in vacuo
10. customThe residue was chromatographed on silica gel using gradient elution (100% hexane to 4/1 hexane/ethyl acetate)