Réaction #2439932

Équation de réaction

9,9-dimethylfluorene-2,7-diboronic acid

2,7-diiodo-9,9-dimethyl fluorene

Na2CO3

HCl

9,9-dimethylfluorene-2,7-diboronic acid

2,7-diiodo-9,9-dimethyl fluorene

→

fluorene

Solvants

toluene

hexane ethyl acetate

THF

THF

Conditions de réaction

Traitement

1. 1
   Autreaccording to synthesis example 1
2. 2
   Autrea Suzuki reaction
3. 3
   workup.ADDITIONby adding
4. 4
   TempératureThereafter, after refluxing for 7 hr
5. 5
   Lavageby washing a toluene phase with water until neutrality
6. 6
   Autreis obtained
7. 7
   SéchageAfter drying with sodium sulfate
8. 8
   Filtrationby filtering
9. 9
   workup.DISTILLATIONdistilling the solvent away
10. 10
    Autrea crude product is obtained
11. 11
    LavageAfter washing with substantially 100 ml of methanol
12. 12
    Autrea colorless crystal is obtained
13. 13
    Autreto remove original components
14. 14
    Autreby recrystallizing

Mode opératoire

With 9,9-dimethylfluorene-2,7-diboronic acid and 2,7-diiodo-9,9-dimethyl fluorene, which are synthesized according to synthesis example 1, a Suzuki reaction is carried out. Under a nitrogen atmosphere, tetrakis(triphenylphosphine)palladium(0) (1.0 mmol) is dissolved in THF (50 ml), followed by adding thereto 2,7-diiodo-9,9-dimethyl fluorene (50 mmol), a solution of 2M Na2CO3 (50 ml) and 9,9-dimethylfluorene-2,7-diboronic acid (25 mmol)/THF (100 ml) in this order. Thereafter, after refluxing for 7 hr, a reaction is brought to an end. The solution is cooled to room temperature, followed by substituting with toluene and adding substantially 30 ml of 1N HCl, further followed by washing a toluene phase with water until neutrality is obtained. After drying with sodium sulfate, followed by filtering and distilling the solvent away, and thereby a crude product is obtained. After washing with substantially 100 ml of methanol, a colorless crystal is obtained. Furthermore, by passing through a short column from hexane/ethyl acetate to remove original components, finally followed by recrystallizing, and thereby fluorene trimer (20 mmol) is obtained.

Source