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DOI: 10.1055/s-2006-942534
A Practical Synthesis of 1,4-Diiodo-2,5-bis(chloromethyl)benzene and 1,4-Diiodo-2,5-bis(bromomethyl)benzene
Publikationsverlauf
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.
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.
11The first synthesis of 1 (ref. 8; also prepared by radical side chain bromination) does not report the product purity.
14Selected 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.
15Selected bond length for 1: I1-C2: 2.096 (3) Å; Cl1-C4: 1.804 (4) Å.