Synthesis of the K-region monofluoro-and difluorobenzo [c] phenanthrenes

S Mirsadeghi, GKB Prasad, N Whittaker…

Index: Mirsadeghi, Seid; Prasad, Ganesh K. B.; Whittaker, Noel; Thakker, Dhiren R. Journal of Organic Chemistry, 1989 , vol. 54, # 13 p. 3091 - 3096

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Citation Number: 20

Abstract

Method A, using 117 mg (0.8 mmol) of o-vanillin, 125 mg (0.85 mmol) of l-bromo-2, 4- pentadiene, and 52 mg (0.8 mmol) of zinc, gave crude alcohol, which was purified by preparative TLC, eluting with 15% ethyl acetate/ligroin to prove 63 mg of product (36% yield). TLC: silica gel, 10% ethyl acetate/ligroin, Rf= 0.17; 20% ethyl acetate/ligroin, R,= 0.47. NMR: 6 3.32 (4, J= 7.5, 1 H), 3.92 (8, 3 H), 2 superimposed doublets 4.88 (J= 7.17) and ...