反应详情

温度

80 °C

A mixture of 2,6-dibromonaphthalene (12.49 g, 43.7 mmol), 2,4-difluorobenzeneboronic acid (3.44 g, 21.8 mmol), sodium carbonate (4.63 g, 45.7 mmol), palladium acetate (245 mg, 1.09 mmol) and tri-o-tolylphosphine (667 mg, 2.19 mmol) in water (15 mL) and ethylene glycol dimethyl ether (90 mL) was degassed and heated to 80° C. overnight. The cooled reaction mixture was partitioned between water and ethyl acetate. The aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over MgSO4 and evaporated in vacuo. The residue was purified by flash column chromatography on silica, eluting with isohexane, to give 2-bromo-6-(2,4-difluorophenyl)naphthalene (1.24 g, contains 10% 2,6-dibromonaphthalene). 1H NMR (500 MHz, CDCl3) δ 8.04 (1H, s), 7.93 (1H, s), 7.82 (1H, d, J=8.5 Hz), 7.75 (1H, d, J=8.6 Hz), 7.62 (2H, dd, J=8.4, 31.8 Hz), 7.50 (1H, m), 7.04-6.91 (2H, m).

1. customwas degassed
2. customThe cooled reaction mixture
3. customwas partitioned between water and ethyl acetate
4. extractionThe aqueous layer was extracted with ethyl acetate
5. washThe combined organic layers were washed with brine
6. dry with materialdried over MgSO4
7. customevaporated in vacuo
8. customThe residue was purified by flash column chromatography on silica
9. washeluting with isohexane