Synthesis 2006(17): 2971-2973  
DOI: 10.1055/s-2006-942534
PSP
© Georg Thieme Verlag Stuttgart · New York

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

Gerald Gaefkea, Volker Enkelmannb, Sigurd Höger*a
a Institut für Technische Chemie und Polymerchemie, Universität Karlsruhe (TH), Engesserstr. 18, 76131 Karlsruhe, Germany
Fax: +49(721)6083153; e-Mail: [email protected];
b Max Planck Institut für Polymerforschung, Ackermannweg 10, 55128 Mainz, Germany
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Publikationsverlauf

Received 17 January 2006
Publikationsdatum:
02. August 2006 (online)

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.

    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.