Hexane → 5-Trimethylstannyl-4,4'-didodecyl-2,2'-bithiophene

HRID 1257981Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1257981
Br[C:2]1[S:6][C:5]([C:7]2[S:8][CH:9]=[C:10]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH:11]=2)=[CH:4][C:3]=1[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35].C([Li])CCC.CCCCCC.[CH3:47][Sn:48](Cl)([CH3:50])[CH3:49]>C1COCC1.C(OCC)C.O>[CH3:47][Sn:48]([CH3:50])([CH3:49])[C:2]1[S:6][C:5]([C:7]2[S:8][CH:9]=[C:10]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH:11]=2)=[CH:4][C:3]=1[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]

Komponenten

8

Edukt 4

HCID 8058HexaneHCID 14016Trimethyltin chlorideHCID 671208205-Bromo-4,4'-didodecyl-2,2'-bithiopheneHCID 178418339Butyllithium

Produkt 1

HCID 575726935-Trimethylstannyl-4,4'-didodecyl-2,2'-bithiopheneAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of 5-bromo-4,4′-didodecyl-2,2′-bithiophene (29A, 100 mg, 0.172 mmol) in 4.0 mL of THF was added dropwise a solution of n-butyllithium in hexane (0.076 mL, 2.5 M, 0.189 mmol) at −78° C. The solution was stirred at −78° C. for 1 hour and a solution of trimethyltin chloride in THF (0.20 mL, 1.0 M, 0.20 mmol) was added in one portion. The solution was warmed to room temperature and 10.0 mL of water and 10.0 mL of diethylether were added. The organic layer was separated and washed twice with 20 mL of water and dried over magnesium sulfate. After filtration, the filtrate was concentrated in vacuo to yield 5-trimethylstannyl-4,4′-didodecyl-2,2′-bithiophene (29, 0.103 g, 90% yield) as a yellow oil. 1H NMR (CDCl3): δ 0.84-1.64 (m, 46H), 2.58 (m, 4H), 6.77 (s, 1H), 6.99 (s, 1H), 7.13 (s, 1H).

Aufarbeitung

  1. temperatureThe solution was warmed to room temperature
  2. customThe organic layer was separated
  3. washwashed twice with 20 mL of water
  4. dry with materialdried over magnesium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-cb0ead2b64da435eb05658c051c743c5
Quelldatensatz
uspto-grants-2013_06
Patentnummer
USRE044304E1

Notizen zur Reaktion

Wird geladen…