Congressane → 4,9-Dibromodiamantane

HRID 374077

Reaktionsgleichung

Reaktionsgleichung von HRID 374077
[CH2:1]1[CH:6]2[CH:7]3[CH:13]4[CH2:14][CH:2]1[CH2:3][CH:4]1[CH:12]4[CH2:11][CH:9]([CH2:10][CH:5]12)[CH2:8]3.[Br-:15].[Al+3].[Br-:17].[Br-]>BrBr>[CH2:14]1[C:2]2([Br:15])[CH2:1][CH:6]3[CH:5]4[CH2:10][C:9]5([Br:17])[CH2:11][CH:12]([CH:4]4[CH2:3]2)[CH:13]1[CH:7]3[CH2:8]5

Komponenten

4

Edukt 2

HCID 123154CongressaneHCID 166749Bromhydrol

Produkt 1

HCID 130222904,9-DibromodiamantaneAusbeute 650,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24408BromineLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Diamantane (50 g, 0.26 mol) was added over 1 h to bromine (200 mL) at 0° C. Aluminum bromide (5.4 g, 0.02 mol) was added and the mixture was stirred at 0° C. for 3 h and at ambient temperature for 16 h. When glc showed less than 5% monobrominated diamantanes, the bromine was removed under reduced pressure and the residue was triturated with pentane (300 mL). The precipitate was filtered, and was washed with pentane (2×150 mL) and methanol (3×100 mL). The residue was recrystallized from toluene to give 45 g (50%) of 4,9-dibromodiamantane, a white solid: mp 328° C. (lit. mp 324°-326° C.); 1H NMR (CDCl3) δ1.97 (s, 6H) 2.31 (s, 12H); 13C NMR (CDCl3) δ39.64, 48.45, 62.81.

Aufarbeitung

  1. customthe bromine was removed under reduced pressure
  2. customthe residue was triturated with pentane (300 mL)
  3. filtrationThe precipitate was filtered
  4. washwas washed with pentane (2×150 mL) and methanol (3×100 mL)
  5. customThe residue was recrystallized from toluene

Quellen und Nachweise

ORD-Eintrag
ord-3fcb860f53e645f6a4374ab41aae2df4
Quelldatensatz
uspto-grants-1992_11
Patentnummer
US05166313

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