Reaction #600495

Reaction equation

phenanthracene-9-boronic acid

THF

2,4-dibromo-1-nitrobenzene

NaOH

→

product

Yield 62.0%

9-(5-bromo-2-nitrophenyl)phenanthrene

Yield 62.0%

Solvents

H2O

Conditions

Workup

1. 1
   workup.DISSOLUTIONthe mixture was dissolved
2. 2
   Otherfollowed by reaction at 80° C. for 24 hours
3. 3
   Extractionthe resultant product was extracted with methylene chloride, water, and brine
4. 4
   Dryingthe organic layer was dried with MgSO4
5. 5
   OtherThe obtained organic layer was purified by silica gel column (methylene chloride:hexane=1:3) so as

Procedure

A 2 L round bottom flask was charged with phenanthracene-9-boronic acid (76.61 g, 345 mmol), THF (700 mL), and H2O (350 mL), and the mixture was dissolved. To the resultant mixture, 2,4-dibromo-1-nitrobenzene (146 g, 518 mmol), NaOH (42 g, 1035 mmol), and Pd(PPh3)4 (20 g, 17.3 mmol) were sequentially added, followed by reaction at 80° C. for 24 hours. After the reaction was completed, the resultant product was extracted with methylene chloride, water, and brine, and the organic layer was dried with MgSO4. The obtained organic layer was purified by silica gel column (methylene chloride:hexane=1:3) so as to give 80.4 g of a product (62%).

Source