反应详情

温度

100 °C

To a stirred mixture of 4-(4-n-pentoxyphenyl)phenylboronic acid (1.0 g, 3.52 mmol) and 4-iodobenzoic acid (874 mg, 3.52 mmol) in ethanol (11 ml) and toluene (30 ml) was added an aqueous solution of sodium carbonate (2M, 5.3 ml, 10.6 mmol) followed by tetrakis-(triphenylphosphine)palladium (204 mg, 5 mol %). The reaction mixture was heated at 100° C. under a nitrogen atmosphere for a period of 18 h. The cooled mixture was acidified to pH 3 (1N HCl) and partitioned between ethyl acetate and water. The organic phase was washed with water (3×) and brine, dried with magnesium sulfate, and filtered through a bed of Celite. The solvent was removed in vacuo to give crude product which was purified by flash silica gel chromatography to provide 4-(n-pentoxyphenyl)-4'-carboxybiphenyl (450 mg): 1H NMR (400 MHz, DMSO-d6) δ 0.89 (t, 3), 1.37 (m, 4 ), 1.72 (m, 2), 3.98 (t, 2), 7.01 (d, 2).

1. custompartitioned between ethyl acetate and water
2. washThe organic phase was washed with water (3×) and brine
3. dry with materialdried with magnesium sulfate
4. filtrationfiltered through a bed of Celite
5. customThe solvent was removed in vacuo
6. customto give crude product which
7. customwas purified by flash silica gel chromatography