1-Bromo-3,5-dimethyladamantane → 3,3',5,5'-Tetramethyl-1,1'-biadamantane

HRID 1433120Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1433120
Br[C:2]12[CH2:11][C:6]3([CH3:12])[CH2:7][CH:8]([CH2:10][C:4]([CH3:13])([CH2:5]3)[CH2:3]1)[CH2:9]2.[Na]>C1(C)C=CC=C(C)C=1>[CH3:8][C:2]12[CH2:9][CH:8]3[CH2:7][C:6]([CH3:12])([CH2:5][C:4]([C:13]45[CH2:13][C:4]6([CH3:10])[CH2:3][CH:2]([CH2:11][C:6]([CH3:12])([CH2:5]6)[CH2:7]4)[CH2:9]5)([CH2:10]3)[CH2:3]1)[CH2:11]2

Komponenten

4

Edukt 2

HCID 983171-Bromo-3,5-dimethyladamantaneHCID 5360545Sodium

Produkt 1

HCID 235969703,3',5,5'-Tetramethyl-1,1'-biadamantane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7929M-XyleneLösungsmittel

Versuchsvorschrift

A coupling reaction of 1-bromo-3,5-dimethyladamantane (Compound A100, product of Aldrich) is caused in m-xylene by the addition of metal sodium, whereby 3,3′,5,5′-tetramethyl-1,1′-biadamantane (Compound A101) is obtained. Compound A101 is then brominated with bromine into a dibromotetramethylbiadamantane derivative (Compound A102). Compound (A102) is reacted with vinyl bromide into Compound A103. The compound A103 is reacted with t-butoxypotassium to obtain 5,5′,7,7′-tetramethyl-3,3′-diethynyl-1,1′-biadamantane (Compound A 104). Moreover, in accordance with the synthesis process shown in <Synthesis of Exemplified compound D-102>, a target Exemplified compound (D-134) (5,5′,7,7′-tetramethyl-3,3′-divinyl-1,1′-biadamantane) is obtained.

Quellen und Nachweise

ORD-Eintrag
ord-c12251917e0845c882f2c7b55699e4b0
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07612155B2

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