反应详情

2,4-Difluoro-phenyl-boronic acid (1.29 g, 8.18 mmol) and 4-iodophenol (0.60 g, 2.7 mmol) were suspended in DMF (60 mL) and 6 mL H2O (6 mL). The mixture was degassed with nitrogen. Finely ground potassium carbonate (1.13 g, 8.18 mmol) and bis(tricyclohexylphosphine) palladium(0) (91 mg, 0.13 mmol) were added. The reaction was stirred at reflux overnight under nitrogen and cooled. The mixture was filtered through a plug of silica gel/Celite and evaporated. The residue was diluted with ethyl acetate and washed with saturated sodium bicarbonate (2×20 mL), dried over MgSO4, filtered and concentrated in vacuo. The crude product was purified by flash chromatography, eluting with 0-25% ethyl acetate in hexanes to yield 2′,4′-difluoro-biphenyl-4-ol (0.61 g, 100%). LR-MS (ES) calculated for C12H8F2O, 206.19; found m/z 205 [M−H]−.

1. customThe mixture was degassed with nitrogen
2. temperatureat reflux overnight under nitrogen
3. temperaturecooled
4. filtrationThe mixture was filtered through a plug of silica gel/Celite
5. customevaporated
6. additionThe residue was diluted with ethyl acetate
7. washwashed with saturated sodium bicarbonate (2×20 mL)
8. dry with materialdried over MgSO4
9. filtrationfiltered
10. concentrationconcentrated in vacuo
11. customThe crude product was purified by flash chromatography
12. washeluting with 0-25% ethyl acetate in hexanes