反应详情

温度

80 °C

Into a 100 mL round bottom flask was added (3-bromo-2-fluoro-4-methoxy-phenyl)-methanol (I-31, 1.04 g, 4.0 mmol), 3-chlorophenylboronic acid (0.76 g, 4.8 mmol), Pd(PPh3)4 (0.45 g, 0.41 mmol), Na2CO3 (6 mL, 2M aq), toluene, (32 mL), and EtOH (11 mL). The reaction was degassed with N2, then stirred at 80° C. for 24 hours. Water was added and the product was extracted with ethyl acetate. The combined organics were concentrated and filtered through a SiO2 plug eluting with 50% ethyl acetate/hexanes. The solid was triturated with ether and filtered. The filtrate was concentrated and triturated with ether and filtered. The filter cakes were combined and purified by flash column chromatography eluting with 20% acetone/hexanes to give (3′-chloro-2-fluoro-6-methoxy-biphenyl-3-yl)-methanol (I-32, 0.79 g, 67%) as a white solid.

1. customThe reaction was degassed with N2
2. additionWater was added
3. extractionthe product was extracted with ethyl acetate
4. concentrationThe combined organics were concentrated
5. filtrationfiltered through a SiO2 plug
6. washeluting with 50% ethyl acetate/hexanes
7. customThe solid was triturated with ether
8. filtrationfiltered
9. concentrationThe filtrate was concentrated
10. customtriturated with ether
11. filtrationfiltered
12. custompurified by flash column chromatography
13. washeluting with 20% acetone/hexanes