Decylbenzene → 1,4-Dibromo-2,5-bis((4-decylphenyl)carbonyl)benzene

HRID 1166024

Reaktionsgleichung

Reaktionsgleichung von HRID 1166024
[Br:1][C:2]1[CH:10]=[C:9]([C:11](Cl)=[O:12])[C:8]([Br:14])=[CH:7][C:3]=1[C:4](Cl)=[O:5].[Cl-].[Al+3].[Cl-].[Cl-].[C:19]1([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(Cl)Cl>[Br:1][C:2]1[CH:10]=[C:9]([C:11]([C:22]2[CH:23]=[CH:24][C:19]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[CH:20][CH:21]=2)=[O:12])[C:8]([Br:14])=[CH:7][C:3]=1[C:4]([C:22]1[CH:21]=[CH:20][C:19]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[CH:24][CH:23]=1)=[O:5]

Komponenten

5

Edukt 3

HCID 7716DecylbenzeneHCID 6451240Aluminum(III) ChlorideHCID 229969282,5-Dibromobenzene-1,4-dicarbonyl dichloride

Produkt 1

HCID 229969271,4-Dibromo-2,5-bis((4-decylphenyl)carbonyl)benzeneAusbeute 74,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Compound 7 (19.2 g, 0.059 mol) was dissolved in 100 mL of dry CH2Cl2, and aluminum chloride (16.6 g, 0.12 mol) was added. The reaction turned orange and some precipitate formed. The reaction was cooled to 0° C., and phenyldecane (45.3 g, 0.21 mol) in 50 mL of dry CH2Cl2 was added through an additional funnel. The reaction was stirred at room temperature under nitrogen overnight. The reaction was quenched carefully with 1 N HCl, extracted with CH2Cl2, and the combined organic phase was dried over MgSO4. The crude product was obtained as off-white solid and was recrystallized from acetone to give 31.8 g of pure product as white crystals at 74% yield. 1H NMR (CDCl3) δ (ppm): 0.88 (t, J=6.7 Hz, 6H), 1.26-1.32 (m, 28H), 1.62-1.67 (m, 4H), 2.69 (t, J=7.6 Hz, 4H), 7.32 (d, J=7.9 Hz, 4H), 7.58 (s, 2H), 7.76 (d, J=7.9 Hz, 4H). Mp 128-129° C.

Aufarbeitung

  1. customsome precipitate formed
  2. customThe reaction was quenched carefully with 1 N HCl
  3. extractionextracted with CH2Cl2
  4. dry with materialthe combined organic phase was dried over MgSO4
  5. customThe crude product was obtained as off-white solid
  6. customwas recrystallized from acetone

Quellen und Nachweise

ORD-Eintrag
ord-6bb04464ee3a436dbb23605c0d87f182
Quelldatensatz
uspto-grants-2003_09
Patentnummer
US06613457B2

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