Reaction #1747845

Reaction equation

triisopropyl borate

hexane

n-butyllithium

hydrochloric acid

9-(3-bromophenyl)phenanthrene

→

3-(9-phenanthrenyl)phenylboronic acid

Yield 67.0%

Solvents

dichloromethane

THF

Conditions

Workup

1. 1
   workup.STIRRINGThen, the reaction mixture was stirred for two hours at −60 degrees C
2. 2
   TemperatureSubsequently, the reaction mixture was warmed up to room temperature
3. 3
   workup.STIRRINGstirred for one hour
4. 4
   workup.WAITThen, the reaction mixture was left for a night
5. 5
   workup.DISTILLATIONThe solvent was distilled away under reduced pressure, such that the reaction mixture
6. 6
   Othercondensed
7. 7
   TemperatureThe reaction mixture was cooled down to 0 degree C
8. 8
   workup.STIRRINGstirred for one hour at room temperature
9. 9
   OtherAfter the reaction
10. 10
    DryingAfter organic phase thereof was dried with magnesium sulfate
11. 11
    workup.DISTILLATIONthe solvent was distilled away under reduced pressure
12. 12
    Otherwas obtained with an yield of 67%

Procedure

Under an argon gas atmosphere, a mixture of 15.45 g (46.4 mmol) of 9-(3-bromophenyl)phenanthrene and 150 mL of dehydrated THF was cooled down to −60 degrees C., and added with 35.9 mL (55.6 mmol) of hexane solution of 1.55M n-butyllithium in drops while being stirred. Then, the reaction mixture was stirred for two hours at −60 degrees C. The reaction solution was added with 26.2 g (139 mol) of triisopropyl borate in drops at −60 degrees C. Subsequently, the reaction mixture was warmed up to room temperature, and stirred for one hour. Then, the reaction mixture was left for a night. The solvent was distilled away under reduced pressure, such that the reaction mixture was condensed. The reaction mixture was cooled down to 0 degree C. to be further added with solution of hydrochloric acid, and then stirred for one hour at room temperature. After the reaction, the reaction mixture was further added with dichloromethane, so that aqueous phase thereof was eliminated. After organic phase thereof was dried with magnesium sulfate, the solvent was distilled away under reduced pressure. Residue thereof was refined by silica-gel column chromatography, such that 13.4 g of 3-(9-phenanthrenyl)phenylboronic acid was obtained with an yield of 67%.

Source