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

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Reaction Steps

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.

Provenance & Evidence