Reaktion #341313

Reaktionsgleichung

compound 2

2-bromo-8,9-dihydro-4H-cyclopenta[def]phenanthrene

4,4,5,5-tetramethyl-2-(10-phenyl-anthracene-9-yl)-[1,3,2]dioxaborolane

K2CO3

THF

→

material 1

2-bromo-cyclopenta[def]phenanthren-4-one

Lösungsmittel

toluene

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe resultant solution was extracted with ethylacetate
2. 2
   TrocknenThe extracted organic phase was dried over anhydrous magnesium sulfate
3. 3
   Filtrationfiltered
4. 4
   Sonstigeto remove a solvent
5. 5
   workup.DISSOLUTIONThe residue was dissolved in a trace amount of toluene
6. 6
   Sonstigepurified on a silica gel column
7. 7
   SonstigeThe resultant solid was recrystallized from toluene and methanol

Vorschrift

The compound 2 (1.0 g, 1 eq., 2.02 mmol), 4,4,5,5-tetramethyl-2-(10-phenyl-anthracene-9-yl)-[1,3,2]dioxaborolane (0.77 g, 1 eq., 2.02 mmol), tetrakis(triphenylphosphine)palladium(0) (0.23 g, 0.1 eq., 0.2 mmol), 2M K2CO3 (1 ml, 1 eq., 2.02 mmol), and tetrabutylammoniumbromide (0.65 g, 1 eq., 2.02 mmol) were put into a 100 ml round bottom flask under an argon gas atmosphere, and THF (50 ml) and toluene (20 ml) were added thereto. The reaction mixture was refluxed at 100° C. for 16 hours. When the reaction solution turned dark brown, water was added, and the resultant solution was extracted with ethylacetate. The extracted organic phase was dried over anhydrous magnesium sulfate and filtered to remove a solvent. The residue was dissolved in a trace amount of toluene and purified on a silica gel column. The resultant solid was recrystallized from toluene and methanol to give a material 1 represented by Formula 18 (0.71 g, 52%). 1H NMR (300 MHz, CDCl3, δ): 8.11 (s, 2H), 7.98 (s, 3H), 7.81 (s, 2H), 7.75-7.10 (m, 13H), 1.93 (m, 4H), 1.21 (m, 20H), 0.87 (m, 6H), 0.65 (broad s, 4H).

Quelle