A Practical Synthesis of 1,4-Diiodo-2,5-bis(chloromethyl)benzene and 1,4-Diiodo-2,5-bis(bromomethyl)benzene

Gerald Gaefke; Volker Enkelmann; Sigurd Höger

doi:10.1055/s-2006-942534

PSP

A Practical Synthesis of 1,4-Diiodo-2,5-bis(chloromethyl)benzene and 1,4-Diiodo-2,5-bis(bromomethyl)benzene

Gerald Gaefke^a, Volker Enkelmann^b, Sigurd Höger*^a
^a Institut für Technische Chemie und Polymerchemie, Universität Karlsruhe (TH), Engesserstr. 18, 76131 Karlsruhe, Germany
Fax: +49(721)6083153; e-Mail: hoeger@uni-bonn.de;
^b Max Planck Institut für Polymerforschung, Ackermannweg 10, 55128 Mainz, Germany

Abstract

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Abstract

Iodination of protected bis(hydroxymethyl)benzene, deprotection of the resulting diiodo aromatics, and subsequent transformation of the hydroxymethyl groups to benzyl halides provides an easy and reliable way to the pure title compounds.

Key words

halogenation - Appel reaction - substituted aromatic alkyl halides - arenes

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References

New adress: Kekulé-Institut für Organische Chemie und Biochemie der Universität Bonn, Gerhard-Domagk-Straße 1, 53121 Bonn, Germany.

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Selected crystal data: 1 (T = 120 K): triclinic, P-1, a = 4.3575 (4), b = 7.2917 (4), c = 8.9994 (5) Å, α = 70.8917 (13), β = 83.3779 (12), γ = 84.9725 (12)°, V = 268.01 (3) Å³, Z = 2, D _x = 2.645 gcm^-3, 5890 independent reflections, 1567 reflections observed, R = 0.0357, R _w = 0.0406. 2 (T = 120 K): triclinic, P-1, a = 4.3865 (4), b = 7.4454 (4), c = 9.0972 (5) Å, α = 71.7302 (13), β = 83.6831 (12), γ = 84.8666 (12)°, V = 279.94 (3) Å³, Z = 1, D _x = 3.059 gcm^-3, 5457 independent reflections, 1454 reflections observed, R = 0.0313, R _w = 0.0345.

Selected bond length for 1: I1-C2: 2.096 (3) Å; Cl1-C4: 1.804 (4) Å.