反应详情

In an oven dried flask flushed with N2 was combined 2.7 g (20.0 mmol) of 3-methylbenzeneboronic acid, 3.64 g (15 mmol) of 2-iodobenzoic acid, 150 mL of DME, 26 mL of 10% Na2CO3 and 600 mg (0.5 mmol) of Pd(PPh3)4. The mixture was warmed to reflux for 24 h and partitioned between 100 mL of NaHCO3 and 100 mL of ether. The ether layer was extracted with 2×50 mL of NaHCO3 and the combined NaHCO3 fractions were washed with 2×50 mL of ether, acidified with 10% HCl and extracted with 3×75 mL of ether. The combined ether extracts were washed with 50 mL of H2O, 50 mL of brine, dried (MgSO4) and concentrated in vacuo. The oil was crystallized from ether/hexanes (1/1) at -20° C. as a white precipitate, which after filtration, provided 1.32 g (41% yield) of 3'-methyl-2-biphenylcarboxylic acid as a brown oil.

1. customIn an oven dried flask
2. customflushed with N2
3. temperatureThe mixture was warmed
4. temperatureto reflux for 24 h
5. custompartitioned between 100 mL of NaHCO3 and 100 mL of ether
6. extractionThe ether layer was extracted with 2×50 mL of NaHCO3
7. washthe combined NaHCO3 fractions were washed with 2×50 mL of ether
8. extractionextracted with 3×75 mL of ether
9. washThe combined ether extracts were washed with 50 mL of H2O, 50 mL of brine
10. dry with materialdried (MgSO4)
11. concentrationconcentrated in vacuo
12. customThe oil was crystallized from ether/hexanes (1/1) at -20° C. as a white precipitate, which
13. filtrationafter filtration