Réaction #2487417

Équation de réaction

2-bromopyridine

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

potassium phosphate tribasic monohydrate

toluene

→

product

Rendement 62.2%

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

Rendement 62.2%

Solvants

water

Conditions de réaction

Traitement

1. 1
   AutreThe reaction mixture was degassed with N2 for 20 minutes
2. 2
   Températurethe reaction mixture was refluxed for 18 h
3. 3
   TempératureAfter cooling
4. 4
   Autrethe aqueous layer was removed
5. 5
   Autretoluene was evaporated under reduced pressure
6. 6
   workup.DISSOLUTIONThe residue was dissolved in dichloromethane
7. 7
   Lavageeluting with dichloromethane
8. 8
   AutreThe crude product was chromatographed on silica gel with 20-25% ethyl acetate in hexane

Mode opératoire

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.

Source