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) δ0.89 (t, 3H), 1.37 (m, 4H), 1.72 (m, 2H), 3.98 (t, 2H), 7.01 (d, 2H).

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