Reaction #531848

Reaction equation

9-(4-Bromophenyl)-10-phenylanthracene

9-phenyl-9H-carbazol-3-boronic acid

tris(o-tolyl)phosphine

potassium carbonate

→

9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazol

Yield 75.0%

Solvents

toluene

1,2-dimethoxyethane

Conditions

Workup

1. 1
   Otherobtained by the above Steps 1(1) to 1(4)
2. 2
   Otherobtained by the above Step 1
3. 3
   TemperatureAfter that, the temperature of this suspending solution was cooled to room temperature
4. 4
   Filtrationthe mixture was filtered
5. 5
   Otherto provide a residue
6. 6
   Filtrationthe mixture was filtered through Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135), alumina, and celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855) while 400 mL of toluene
7. 7
   workup.ADDITIONwas added
8. 8
   Othercondensed, hexane
9. 9
   workup.ADDITIONwas added
10. 10
    Otherrecrystallization
11. 11
    Otherthe object of the synthesis
12. 12
    Otherwas obtained in a yield of 75% (synthesis scheme (b-2))

Procedure

In a 200 mL three-neck flask were stirred 1.9 g (4.7 mmol) of 9-(4-Bromophenyl)-10-phenylanthracene (abbreviation: PA) obtained by the above Steps 1(1) to 1(4) described in Synthesis Example 1, 1.4 g (4.7 mmol) of 9-phenyl-9H-carbazol-3-boronic acid obtained by the above Step 1 described in Synthesis Example 2, 5.6 mg (25 μmol) of Palladium(II) acetate (abbreviation: Pd(OAc)2), 52 mg (170 μmol) of tris(o-tolyl)phosphine (abbreviation: P(o-tolyl)3), 7 mL (15 mmol) of potassium carbonate aqueous solution (2.0 mol/L), and 40 mL of 1,2-dimethoxyethane (abbreviation: DME) in a nitrogen atmosphere for 7 hours while being heated at 90° C. After that, the temperature of this suspending solution was cooled to room temperature, and the mixture was filtered to provide a residue. The obtained residue was dissolved into 50 mL of hot toluene, and the mixture was filtered through Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135), alumina, and celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855) while 400 mL of toluene was added. The obtained filtrate was condensed, hexane was added therein, ultrasonic waves were applied thereto, and then recrystallization thereof was performed. Accordingly, 2.0 g of a powdery light-yellow solid of 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazol (abbreviation: PCzPA), which was the object of the synthesis, was obtained in a yield of 75% (synthesis scheme (b-2)).

Source