Process for producing 4,9-dibromodiamantane

Details Process for producing 4,9-dibromodiamantane Process for producing 4,9-dibromodiamantane

2011-01-18

2011-01-18

Parsa, Jafar (Department: 1621)

Organic compounds -- part of the class 532-570 series

Organic compounds

Halogen containing

C570S252000

Reexamination Certificate

active

07872164

ABSTRACT:
A process for selectively producing 4,9-dibromodiamantane includes a step of reacting diamantane with bromine in the presence of a Lewis acid and a solvent, wherein the solvent comprises a substituted or unsubstituted, straight-chain, branched-chain or cyclic saturated hydrocarbon containing from 3 to 10 carbon atoms, and a reaction solution after the step satisfies Formula (1):in-line-formulae description="In-line Formulae" end="lead"?A/(A+B+C+D+E)>0.80   Formula (1)in-line-formulae description="In-line Formulae" end="tail"?wherein A represents an area ratio (%) of 4,9-dibromodiamantane obtained by gas chromatography of the reaction solution, B represents an area ratio of diamantane, C represents a sum of an area ratio of 1-bromodiamantane and an area ratio of 4-bromodiamantane, D represents an area ratio of tribromodiamantane, and E represents a sum of an area ratio of 1,6-dibromodiamantane and an area ratio of 1,4-dibromodiamantane.

REFERENCES:
patent: 2005/0276964 (2005-12-01), Watanabe et al.
Matthew C. Davis, selective apical bromination of diamantane and conversion to the dihydroxy and dicarboxylic acid derivatives, Synthetic Communication, 36, 3509-3515, 2006.
T.M. Gund et al: “The Functionalization of Diamantane”. Tetrahedron Lett., No. 56, 1970, pp. 4875-4878, XP002467813.
T.M.Gund: “The ionic bromination of diamantane”, Tetrahedron Lett., No. 19, 1971, pp. 1583-1586, XP002467814.
T.M.Gund: “Diamantane. III Preparation and solvolysis of diamantyl bromides”, J.Org.Chem., vol. 39, No. 20, 1974, pp. 2995-3003, XP002467815.
T. M. Gund et al.“Diamantane.II. Preparation of derivatives of diamantane”, Journal of Organic Chemistry, vol. 39 No. 20, 1974 pp. 2987-2994.

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