反应详情

温度

80 °C

A biphasic mixture of 3-bromofuran (2.90 mL, 32.1 mmol), benzene (70 mL), and 2N aqueous Na2CO3 (50 mL) was degassed and purged with argon. Tetrakis(triphenylphosphine) palladium(0) (3.7 g, 3.2 mmol) arid a solution of 4-biphenylboronic acid (6.3 g, 32.1 mmol) in EtOH (50 mL) were added sequentially. The mixture was heated at 80° C. for 18 hours, allowed to cool, and partitioned between CH2Cl2 and H2O. The aqueous layer was separated and extracted with CH2Cl2 two times. The combined organic layers were washed with brine, dried over Na2SO4, and concentrated to a crude product, which was dissolved in a minimal amount of CH2Cl2 and applied to a flash chromatography column packed with hexanes. Elution with 10% CH2Cl2/hex led to some mixed fractions, which were rechromatographed. A total of 5.37 g (76%) of 3-(biphenyl-4-yl)furan was obtained as a pale yellow oil.

1. customwas degassed
2. custompurged with argon
3. additionwere added sequentially
4. temperatureto cool
5. custompartitioned between CH2Cl2 and H2O
6. customThe aqueous layer was separated
7. extractionextracted with CH2Cl2 two times
8. washThe combined organic layers were washed with brine
9. dry with materialdried over Na2SO4
10. concentrationconcentrated to a crude product, which
11. dissolutionwas dissolved in a minimal amount of CH2Cl2
12. washElution with 10% CH2Cl2/hex
13. customwere rechromatographed