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■ Oxidative Coupling Reaction of 2-Halophenols with K₃Fe(CN)₆ in Benzene Solution

Masashi Tashiro and Haruo Yoshiya

*Research Institute of Industrial Science, Faculty of Engineering, Kyushu University, 6-1, Kasuga-koen, Kasuga 816-8580, Japan

Abstract

The oxidative coupling of twelve 2-halophenols (1a-1l) was carried out with K₃Fe(CN)₆ in benzene solution to obtain the corresponding dibenzofuran derivatives. However, only a small amount of the desired dibenzofurans such as 2,6-di-tert-butyl-8-methoxydibenzofuran-1,4-quinone (9) and 4,8-di-tert-butyl-2,6-di-isopropyl-1-hydroxydibenzofuran (11) were obtained from 2-bromo-6-tert-butyl-4-methoxy- (1d) and 2-bromo-4-tert-butyl-6-isopropylphenol (1g), respectively. In the other cases, alternative type of products or tarry materials were formed.