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

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Synthesis 2006(17): 2971-2973
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

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Publication History

Received 17 January 2006
Publication Date:
02 August 2006 (online)

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

References

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1

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

11

The first synthesis of 1 (ref. 8; also prepared by radical side chain bromination) does not report the product purity.

14

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.

15

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