Bromination of Acetophenone using N-Bromosuccinimide
Keywords:
bromination, bromoketones, intermediatesAbstract
Acetophenone react with N-bromosuccinimide and p-toluenesulphonic acid (p-TsOH) using acetonitrile as a solvent to yield α-bromoacetophenone in high yields. The reaction does not take place in the absence of p-TsOH. However, the reaction is possible photochemically even in the absence of p-TsOH.
References
Prakash, O.; Kumar, A.; Sadana, A.; Singh, S. P. A facile synthesis of 3,4-dihydro-2-pyronyl-1,5-benzodiazepine derivatives. Synth. Commun. 2002, 32, 2663-2667.
Prakash, R.; Kumar, A.; Singh, S. P.; Aggarwal, R. Dehydroacetic acid and its derivatives in organic synthesis: synthesis of some new 2-substituted-4-(5-bromo-4-hydroxy-6-methyl-2H-pyran-2-one-3-yl)thiazoles. Indian J. Chem. Section B: Org. Chem. Including medicinal chem. 2007, 46B, 1713-1715.
Harris, T. M.; Harris, C. W.; Brush, C. K. Bromination of dehydroacetic acid. J. Org. Chem. 1970, 35, 1329-1333.
Kumar, A.; Prakash, R.; Singh, S. P.; Prakash, O. Synthesis of 3β,3β,5-tribromoacetyl-4-hydroxy-6-methyl-2H-pyran-2-one by bromination of DHA. Synth. Commun. 2005, 35, 461.
Clark, J.H. Green Chemistry: challenges and opportunities. Green Chem. 1999, 1, 1-8.
Anastas, P.T.; Warner, J.C (2000) Green Chemistry Theory and Practice. Oxford University Press, Oxford, U.K. 2000, 20-33.
Lidstrom, P.; Tierney, J.; Wathey, B.; Westman, J. Microwave assisted organic synthesis – a review. Tetrahedron. 2001, 57, 9225.
Nuchter, M.; Ondruschka, B.; Bonrath W.; Gum, A. Microwave assisted synthesis – a critical technology overview. Green Chem. 2004, 6, 128-141.
Goswami, S.; Dey, S.; Jana, S.; Adak, A.K. Side chain bromination of mono and dimethyl heteroaromatic and aromatic compounds by solid phase N-bromosuccinimide reaction without radical initiator under microwave. Chem. Lett. 2004, 33, 916-917.
Kuang, C.; Yang, Q.; Senboku, H.; Tokuda, M. Synthesis of (Z)-1-bromo-1-alkenes and terminal alkynes from anti-2, 3-dibromoalkanoic acids by microwave-induced reaction. Tetrahedron. 2005, 61, 4043-4052.
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