A Convenient and Unambiguous Synthesis of 2(or 7)-Chloronaphthalenes from Substituted α-Tetralones

Article abstract of DOI:10.1055/s-1989-27317

2(or 7)-Chloronaphthalenes 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.