A revised synthesis of 5-methylbenz(a)anthracene is reported. It involves only three simple and convenient steps starting from a commercially available compound, and gives a 82% overall yield. Bromination of 5-methylbenz(a)anthracene with N-bromosuccinimide (NBS) in carbon tetrachloride furnishes 5-bromomethylbenz(a)anthracene in a 92% yield. When bromination is carried out using dimethylformamide as the solvent, 7-bromo-5-methylbenz(a)anthracene is formed as the exclusive product.
Che, Jia and Yang, Dominic T.C.
"Improved Synthesis of 5-methylbenz(a)anthracene,"
Journal of the Arkansas Academy of Science: Vol. 41
, Article 8.
Available at: http://scholarworks.uark.edu/jaas/vol41/iss1/8