Water → 5-Bromo-4,4'-didodecyl-2,2'-bithiophene

HRID 1257980

Reaktionsgleichung

Reaktionsgleichung von HRID 1257980
[CH2:1]([C:13]1[CH:14]=[C:15]([C:18]2[S:19][CH:20]=[C:21]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH:22]=2)[S:16][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].C1C(=O)N([Br:42])C(=O)C1.O>C(Cl)(Cl)Cl.CC(O)=O>[Br:42][C:20]1[S:19][C:18]([C:15]2[S:16][CH:17]=[C:13]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH:14]=2)=[CH:22][C:21]=1[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]

Komponenten

5

Edukt 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 219172654,4'-Didodecyl-2,2'-bithiophene

Produkt 1

HCID 671208205-Bromo-4,4'-didodecyl-2,2'-bithiopheneAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21584526Acetic acid chloroformLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 4,4′-didodecyl-2,2′-bithiophene (0.100 g, 0.199 mmol) in CHCl3/HOAc (1:1) (Vt=2.0 mL) at 0° C. was added N-bromosuccimide (NBS, 35.7 mg, 0.199 mmol) in portions over a period of 45 minutes. The reaction mixture was stirred for 1 hour at 0° C. and overnight at room temperature. The reaction mixture was poured into water (50.0 mL) and extracted with chloroform (3×50.0 mL). The combined organic phases were washed with water (50.0 mL), NaOH solution, and dried over MgSO4. After filtration through Celite, the filtrate was concentrated in vacuo and the residue was purified by column chromatography on silica gel (hexanes) to provide 5-bromo-4,4′-didodecyl-2,2′-bithiophene (29A) as a colorless oil (98.0 mg, 85% yield). 1H NMR (CDCl3): δ 0.84-1.54 (m, 46H), 2.57 (m, 4H), 6.81 (s, 1H), 6.84 (s, 1H), 6.94 (s, 1H).

Aufarbeitung

  1. extractionextracted with chloroform (3×50.0 mL)
  2. washThe combined organic phases were washed with water (50.0 mL), NaOH solution
  3. dry with materialdried over MgSO4
  4. filtrationAfter filtration through Celite
  5. concentrationthe filtrate was concentrated in vacuo
  6. customthe residue was purified by column chromatography on silica gel (hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-76cd16eac47841e4bc50a1a442274da4
Quelldatensatz
uspto-grants-2013_06
Patentnummer
USRE044304E1

Verknüpfte Notizen

Wird geladen…