Iodine → 5,6-Dioctylnaphtho[2,1-b:3,4-b']dithiophene

HRID 713601Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 713601
[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[C:11]([C:12]3[CH:16]=[CH:15][S:14][CH:13]=3)=[CH:10][C:9]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[C:8]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH:7]=2)=[CH:2]1.II>C1(C)C=CC=CC=1.[Hg]>[CH2:17]([C:9]1[CH:10]=[C:11]2[C:12]3[CH:16]=[CH:15][S:14][C:13]=3[C:2]3[S:1][CH:5]=[CH:4][C:3]=3[C:6]2=[CH:7][C:8]=1[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Komponenten

5

Edukt 2

HCID 807IodineHCID 580989504,5-Bis(3-thienyl)-1,2-dioctylbenzene

Produkt 1

HCID 580989305,6-Dioctylnaphtho[2,1-b:3,4-b']dithiopheneAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23931MercuryKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

In a quartz tube was added a solution of 4,5-bis(3-thienyl)-1,2-dioctylbenzene (0.5 g, 1.1 mmol) and iodine (30 mg) in toluene (500 mL). The system was then irradiated by a 400 W mercury lamp equipped with an efficient cooling system for 16 hours under magnetic stirring and air bubbling. The reaction mixture was washed with a saturated aqueous solution of Na2S2O3, dried over MgSO4 and concentrated. The residue was purified by flash chromatography on silica gel (hexane as eluent), and a white solid was obtained (0.33 g, yield: 65%). mp: 62.2-63.1° C. 1H NMR (400 MHz, CDCl3) δ 8.11 (s, 2H), 7.97 (d, 2H), J=5.34 Hz), 7.47 (d, 2H, J=5.30), 2.86 (t, 4H, J=7.76 Hz), 1.74 (m, 4H), 1.32-1.50 (m, 20H), 0.92 (t, 6H), J=6.80 Hz). 13C NMR (400 MHz, CDCl3) δ 139.22, 134.12, 131.25, 126.09, 124.04, 123.34, 122.74, 33.14, 31.29, 31.52, 29.86, 29.58, 29.34, 22.70, 14.14. MS: m/z=464.4 [M]+ (Calcd.: 464.2).

Aufarbeitung

  1. customequipped with an efficient cooling system for 16 hours
  2. customair bubbling
  3. washThe reaction mixture was washed with a saturated aqueous solution of Na2S2O3
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography on silica gel (hexane as eluent)
  7. customa white solid was obtained (0.33 g, yield: 65%)

Quellen und Nachweise

ORD-Eintrag
ord-c8ba8af15fb44dc0820dd980c43b4e32
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09184390B2

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