Reaction #976967

Reaction equation

benzo[g]chrysene-10-boronic acid

3-bromoiodobenzene

sodium carbonate

→

10-(3-bromophenyl)benzo[g]chrysene

Yield 95.0%

Solvents

toluene

Conditions

Workup

1. 1
   Otherwere placed in a flask
2. 2
   TemperatureThe resultant was refluxed
3. 3
   Extractionthe reaction solution was extracted with toluene
4. 4
   OtherAn aqueous phase was removed
5. 5
   Otheran organic phase which had been separated
6. 6
   Washwas washed with water
7. 7
   Dryingwith saturated brine, and dried with magnesium sulfate
8. 8
   FiltrationAfter the magnesium sulfate was filtered out
9. 9
   Concentrationthe organic phase was concentrated
10. 10
    OtherThe resulting residue was purified by a silica gel column chromatography

Procedure

Under an argon atmosphere, 3.86 g of the benzo[g]chrysene-10-boronic acid which had been prepared in Synthesis Example 3, 2.83 g of 3-bromoiodobenzene, 0.231 g of tetraxis(triphenylphosphine)palladium(0), 40 mL of toluene and 20 mL of a 2M aqueous solution of sodium carbonate were placed in a flask. The resultant was refluxed with stirring for 8 hours. After cooling to room temperature, the reaction solution was extracted with toluene. An aqueous phase was removed, and an organic phase which had been separated was washed with water and then with saturated brine, and dried with magnesium sulfate. After the magnesium sulfate was filtered out, the organic phase was concentrated. The resulting residue was purified by a silica gel column chromatography, whereby 4.12 g (yield: 95%) of 10-(3-bromophenyl)benzo[g]chrysene was obtained.

Source