Reaction #1747844

Reaction equation

9-phenanthreneboronic acid

3-bromoiodobenzene

sodium carbonate

→

9-(3-bromophenyl)phenanthrene

Yield 74.0%

Solvents

toluene

water

dimethoxyethane

toluene

Conditions

Workup

1. 1
   Temperaturewhile being refluxed
2. 2
   OtherAfter the reaction
3. 3
   DryingAfter organic phase thereof was dried with magnesium sulfate
4. 4
   workup.DISTILLATIONthe toluene was distilled away under reduced pressure
5. 5
   Otherwas obtained with an yield of 74%

Procedure

Under an argon gas atmosphere, 31.4 g (141 mmol) of 9-phenanthreneboronic acid, 40.0 g (141 mmol) of 3-bromoiodobenzene, 3.30 g (2.83 mmol) of tetrakis(triphenylphosphine) palladium(0), 200 mL of toluene, 50 mL of dimethoxyethane and 212 mL of 2M sodium carbonate solution were mixed, and stirred for four hours while being refluxed. After the reaction, the reaction mixture was further added with toluene, and cleansed by water. After organic phase thereof was dried with magnesium sulfate, the toluene was distilled away under reduced pressure. Residue thereof was refined by silica-gel column chromatography, such that 34.7 g of 9-(3-bromophenyl)phenanthrene was obtained with an yield of 74%.

Source