Synthesis of 3-bromocyclohexene

Preparation of 3-bromocyclohexene

Preparation of 3-bromocyclohexene

Preparation of 3-bromocyclohexene

0.1 mole of dry cyclohexene (dried by boiling over phosphorus pentoxide for 1 hour and distill) is dissolved in 100 ml of carbon tetrachloride that has been dried over phosphorus pentoxide, and is treated with 0.1 mole of dry N-bromosuccinimide and 2.2 g of azo-bis-isobutyronitrile. This mixture is carefully boiled under reflux in a round-bottomed flask until the reaction begins, as shown by the evolution of heat (more vigorous boiling). Although some cooling must then be applied, care must be taken that the reaction is not stopped. The end of the reaction can be seen from the fact that the denser N-bromosuccinimide has dissolved and been converted into succinimide, which floats on the surface. To ensure completion of the reaction, the mixture is boiled another 1 hour (the bromination reaction may take longer!). After cooling, the succinimide is filtered off and washed with a little carbon tetrachloride, and the carbon tetrachloride is distilled off from the combined filtrates under a vacuum. The residue is purified by distillaion in vacuo. The yield of 3-bromocyclohexene is 40%, b.p.75°C/16mm; 57-58 °C/12 mm; n20/D 1.5285; d=1.4 g/mL at 25 °C.

Organicum. Practical Handbook of Organic Chemistry, by Heinz Becker, Werner Berger and Günter Domschke, Addison-Wesley Pub. Co, 174-175, (1973)

IUPAC Name

3-bromocyclohexene

InChI

InChI=1S/C6H9Br/c7-6-4-2-1-3-5-6/h2,4,6H,1,3,5H2

InChI Key

AJKDUJRRWLQXHM-UHFFFAOYSA-N

Canonical SMILES

C1CC=CC(C1)Br

Depositor-Supplied Synonyms

3-Bromocyclohexene, 3-Bromocyclohex-1-ene, 1521-51-3, Cyclohexene, 3-bromo-, 1-Bromo-2-cyclohexene, 3-Bromo-1-cyclohexene, 3-bromo-cyclohexene, 1,2,3,4-Tetrahydrobromobenzene, 2-Cyclohexen-1-yl bromide, AJKDUJRRWLQXHM-UHFFFAOYSA-N, SBB007864, 3-bromo cyclohexene, 3-bromanylcyclohexene, 2-Cyclohexenyl bromide, 1-bromocyclohex-2-ene, ACMC-1BOD5, AC1L39ST, AC1Q26CQ, AC1Q26CR, KSC172O0B, SCHEMBL239631, 333549_ALDRICH, CTK0H2700, MolPort-001-790-644, CYCLOHEXENE,3-BROMO-,(R)-, ANW-21386, AKOS015919783, RP22383, AK-78901, AN-49372, BR-78901, KB-30559, OR012763, OR101962, OR204327, R943, SC-88440, AB0018412, RT-000752, AM20080711, B0943, FT-0615221, ST24041968, ST50405878, EN300-67511, S-4971, A809268, S14-0706, 3B3-050096, 108055-90-9

Removed Synonyms

C6H9Br, CID137057

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