Water → 3-Bromo-7-methylphenanthrene

Participants

Reaction Steps

A stirred mixture of 3-Bromo-7-methyl-phenanthrene-9-carboxylic acid (5.50 g, 17.5 mmol) and CuCO3.Cu(OH)2.H2O (1.5 g) in 50 ml of quinoline was rapidly heated to 210° C. Gas evolution was observed and the mixture became extremely dark. After 10 min the mixture was allowed to cool to room temperature and was diluted with PhCH3 --CH2Cl2 (9:1) and filtered. The filtrate was washed with 1N HCl (2x) and brine. Drying (Na2SO4) and evaporation gave 4.89 g of a brown oil which was flash chromatographed through 450 g of silica gel (10% CH2Cl2 /hexane) to yield 2.63 g (56%) of the title compound as a pale yellow solid.

Provenance & Evidence