J. D. Prugh, A. Deana, J. M. Wiggins
1989
Citations
0
Influential Citations
11
Citations
Journal
Synthesis
Abstract
2 (or 7)-Chlornaphthalenes are unambiguously prepared from α-tetralones (1-oxo-1,2,3,4-tetrahydronaphthalenes) by introducing two chlorines in the 2-position with sulfuryl chloride, reducing the ketone with sodium borohydride, and then converting the resulting hydroxy to chloro with thionyl chloride. Vicinal chlorines are then removed with activated zinc giving a vinyl chloride which is aromatized with 2,3-dichloro-4,5-dicyano-1,4-benzoquinone (DDQ) to give the desired 2 (or 7)-chloronaphthalenes