反应详情

温度

80 °C

A mixture of 250 mg (1.09 mmol) of 4-bromo-3-methyl-benzoic acid methyl ester, 204 mg (1.31 mmol) of 4-chlorophenylboronic acid, 1.06 g (3.27 mmol) of cesium carbonate (Cs2CO3) and PdCl2(dppf) catalyst (5 mol %) was flushed with argon. To this mixture was added 3 mL of 1,4-dioxane and the reaction mixture was heated to 80° C. overnight. The mixture was then cooled to rt, and filtered through a pad of Celite while rinsing the pad with ethyl acetate. The filtrate was washed with brine, dried over sodium sulfate and concentrated to give a residue which was chromatographed on silica gel (5% ethyl acetate in hexane) to afford 191 mg (67%) of desired 4′-chloro-2-methyl-biphenyl-4-carboxylic acid methyl ester, as an oil as indicated by 1H NMR; LC-MS calcd for C15H13ClO2 [M++H]+: 261.07, found: 261.1.

1. customwas flushed with argon
2. additionTo this mixture was added 3 mL of 1,4-dioxane
3. temperatureThe mixture was then cooled to rt
4. filtrationfiltered through a pad of Celite
5. washwhile rinsing the pad with ethyl acetate
6. washThe filtrate was washed with brine
7. dry with materialdried over sodium sulfate
8. concentrationconcentrated
9. customto give a residue which
10. customwas chromatographed on silica gel (5% ethyl acetate in hexane)