반응 #2487417

반응 방정식

2-bromopyridine

dibenzo[b,d]furan-4-ylboronic acid

potassium phosphate tribasic monohydrate

toluene

→

product

수율 62.2%

4-(2-pyridyl)dibenzo[b,d]furan

수율 62.2%

용매

water

반응 조건

후처리

1. 1
   기타The reaction mixture was degassed with N2 for 20 minutes
2. 2
   온도the reaction mixture was refluxed for 18 h
3. 3
   온도After cooling
4. 4
   기타the aqueous layer was removed
5. 5
   기타toluene was evaporated under reduced pressure
6. 6
   workup.DISSOLUTIONThe residue was dissolved in dichloromethane
7. 7
   세척eluting with dichloromethane
8. 8
   기타The crude product was chromatographed on silica gel with 20-25% ethyl acetate in hexane

실험 절차

To a 1 L round-bottom flask was added 2-bromopyridine (13.80 mL, 142 mmol), dibenzo[b,d]furan-4-ylboronic acid (25 g, 118 mmol), dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine (1.936 g, 4.72 mmol) and potassium phosphate tribasic monohydrate (81 g, 354 mmol) with toluene (350 mL) and water (35 mL). The reaction mixture was degassed with N2 for 20 minutes. Pd2(dba)3 (2.16 g, 2.35 mmol) was added and the reaction mixture was refluxed for 18 h. Completion of the reaction was confirmed by HPLC, GC and TLC. After cooling, the aqueous layer was removed and toluene was evaporated under reduced pressure. The residue was dissolved in dichloromethane and passed through one inch silica gel plug on a frit, eluting with dichloromethane. The crude product was chromatographed on silica gel with 20-25% ethyl acetate in hexane to give 18 g (62%) of the product. The product was confirmed by HPLC (99.6% purity) and GC/MS.

출처