4-Bromobenzocyclobutene
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4-Bromobenzocyclobutene
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CAS No:
1073-39-8
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Formula:
C8H7Br
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Chemical Name:
4-Bromobenzocyclobutene
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CAS No:
4-Bromobenzocyclobutene Use and Manufacturing
The synthesis of a tetracene brominated in the 2-position is shown by way of example in the following illustration: In a first step, α-chloro-o-xylene 1 was subjected to pyrolysis at approximately 800° C. and 0.5 mbar. Benzocyclobutene 2 was obtained in a 45percent yield. The selective bromination thereof was carried out by treating benzocyclobutene, dissolved in acetic acid, with a mixture of bromine and iodine at room temperature, resulting in 4-bromobenzocyclobutene 3. Dissolving in toluene and heating with a slight molar excess of 1, 4-dihydro-1, 4-epoxynaphthalene 4 at 220° C. for 20 hours resulted in an 80percent yield of a pure endo/exo mixture of the Diels-Alder addition product 5, a colorless crystalline material. This material was heated at reflux in acetic anhydride in the presence of concentrated hydrochloric acid, thus forming 9-bromo-6, 11-dihydrotetracene 6. The Yamamoto coupling then resulted in 2-(5, 12-dihydrotetracene-2-yl)-5, 12-dihydrotetracene 7. The coupling reaction was carried out in an approximately 80percent yield in a mixture of dimethylformamide and toluene at 80° C., using bis(cyclooctadienyl) nickel(0) in stoichiometric quantities. After recrystallization from o-dichlorobenzene, compound 7 was dehydrogenated by treatment with 2, 3-dichloro-5, 6-dicyano-p-benzoquinone (DDQ) in boiling o-xylene. After purification by repeated vacuum sublimation, orange-red crystals of 2-(tetracene-2-yl) tetracene 8 were obtained in a yield of 75percent. All intermediate products were characterized by
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