Sodium Carbonate → 9,9-Bis[3-ethoxycarbonyl-4-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]phenyl]-fluorene

Temperatur

105 °C

In an inert atmosphere, the compound A (0.55 g), the compound B (0.61 g), (triphenylphosphine)palladium (0.01 g), methyltrioctylammonium chloride (manufactured by Aldrich Co.; trade name: Aliquat 336 (registered trademark)) (0.20 g), and toluene (10 mL) were mixed, and the resultant reaction mixture was heated to 105° C. Into the reaction solution, a 2 mol/L sodium carbonate aqueous solution (6 mL) was added dropwise, and the resultant reaction mixture was refluxed for 8 hours. To the reaction solution, 4-tert-butylphenylboronic acid (0.01 g) was added, and the resultant reaction mixture was refluxed for 6 hours. Next, to the reaction mixture, a sodium diethyldithiocarbamate aqueous solution (10 mL, concentration: 0.05 g/mL) was added, and the resultant reaction mixture was stirred for 2 hours. The resultant solution mixture was added dropwise into 300 mL of methanol, and the resultant reaction mixture was stirred for 1 hour. Then, a deposited precipitate was filtered and the precipitate was dried under reduced pressure for 2 hours, followed by dissolving the precipitate in 20 mL of tetrahydrofuran. The resultant reaction solution was added dropwise into a solvent mixture of 120 mL of methanol and 50 mL of a 3% by weight acetic acid aqueous solution, and the resultant reaction mixture was stirred for 1 hour. A deposited precipitate was filtered, and the precipitate was dissolved in 20 mL of tetrahydrofuran. The thus obtained reaction solution was added dropwise into 200 mL of methanol, and the resultant reaction mixture was stirred for 30 minutes. A deposited precipitate was filtered to obtain a solid. The obtained solid was dissolved in tetrahydrofuran, and the resultant solution was passed through an alumina column and a silica gel column to purify the solution. The tetrahydrofuran solution recovered from the column was concentrated, and the concentrate was added dropwise into methanol (200 mL), followed by filtering and drying a deposited solid. The yield of obtained poly[9,9-bis[3-ethoxycarbonyl-4-bis[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]phenyl]-fluorene] (polymer A (BSAFEGP)) was 520 mg.

1. customthe resultant reaction mixture
2. customthe resultant reaction mixture
3. temperaturewas refluxed for 8 hours
4. customthe resultant reaction mixture
5. temperaturewas refluxed for 6 hours
6. customthe resultant reaction mixture
7. customthe resultant reaction mixture
8. stirringwas stirred for 1 hour
9. filtrationThen, a deposited precipitate was filtered
10. customthe precipitate was dried under reduced pressure for 2 hours
11. dissolutionby dissolving the precipitate in 20 mL of tetrahydrofuran
12. customThe resultant reaction solution
13. customthe resultant reaction mixture
14. stirringwas stirred for 1 hour
15. filtrationA deposited precipitate was filtered
16. dissolutionthe precipitate was dissolved in 20 mL of tetrahydrofuran
17. customThe thus obtained reaction solution
18. customthe resultant reaction mixture
19. stirringwas stirred for 30 minutes
20. filtrationA deposited precipitate was filtered
21. customto obtain a solid
22. customa silica gel column to purify the solution
23. customThe tetrahydrofuran solution recovered from the column
24. concentrationwas concentrated
25. additionthe concentrate was added dropwise into methanol (200 mL)
26. filtrationby filtering
27. customdrying a deposited solid

ORD-Eintrag

ord-f8f9145c562b41d6ba22f210a09c72ba

Quelldatensatz

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09006008B2