Reaction #955947

Reaction equation

HCl

BuLi

9-Bromophenanthrene

Me2SO4

→

product

9-methylphenanthrene

Solvents

ether

ether

Conditions

Workup

1. 1
   TemperatureThe reaction mixture was warmed to room temperature
2. 2
   Temperaturewas cooled to −78° C. again
3. 3
   workup.STIRRINGThe mixture was stirred at room temperature for 10 h
4. 4
   Extractionextracted with CH2Cl2
5. 5
   Dryingdried over MgSO4
6. 6
   OtherThe solvent was evaporated
7. 7
   Otherto give a residue which
8. 8
   Otherwas recrystallized from hexane

Procedure

9-Bromophenanthrene (27 g, 102 mmol) was dissolved in 400 mL of dry ether and cooled to −78° C. 170 mL of BuLi (1.6 M in hexane) was slowly added into this solution in 45 minutes. The reaction mixture was warmed to room temperature. The mixture was then stirred at room temperature for 2 h before it was cooled to −78° C. again and Me2SO4 (17.6 g, 133 mmol) in ether was slowly added. The mixture was stirred at room temperature for 10 h. The mixture was poured into 15% HCl aqueous solution and extracted with CH2Cl2 and dried over MgSO4. The solvent was evaporated to give a residue which was recrystallized from hexane to yield 14.2 g of product as a white solid.

Source