1,3-Dibromobenzene → 2-(3-bromophenyl)furan

1,3-Dibromobenzene (1.0 g) was dissolved in toluene (20 ml), the solution was added with tri-n-butyl-(2-furyl)tin 1.59 g) and tetrakistriphenylphosphine palladium (0.25 g), and the mixture was stirred for 30 minutes under reflux by heating. The reaction mixture was concentrated under reduced pressure, and then the residue was dissolved in hexane. The solution was filtered through silica gel, and the filtrate was concentrated under reduced pressure. The resulting residue was dissolved in diethyl ether, the solution was added with cesium fluoride (1.01 g), and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was added with a mixed solvent of hexane:ethyl acetate=10:1, and the mixture was filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane alone) to obtain the title compound (0.59 g).

1. temperatureunder reflux
2. temperatureby heating
3. concentrationThe reaction mixture was concentrated under reduced pressure
4. dissolutionthe residue was dissolved in hexane
5. filtrationThe solution was filtered through silica gel
6. concentrationthe filtrate was concentrated under reduced pressure
7. dissolutionThe resulting residue was dissolved in diethyl ether
8. additionthe solution was added with cesium fluoride (1.01 g)
9. stirringthe mixture was stirred at room temperature for 30 minutes
10. additionThe reaction mixture was added with a mixed solvent of hexane
11. filtrationethyl acetate=10:1, and the mixture was filtered
12. concentrationThe filtrate was concentrated under reduced pressure
13. customthe resulting residue was purified by silica gel column chromatography (hexane alone)

ORD record

ord-402fffcd5878420586152774bbd5ed6c

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08097708B2