Behavior of Bromine Derivatives of Guaiacol toward Nitrating Agents

Abstract

Attempts to nitrate 4, 5, 6-tribromoguaiacol by means of nitrous acid as directed by Zincke failed to give any product that could be identified. The use of nitric acid of various concentrations also failed to give more than traces of nitro product. Treatment of the acetyl and benzoyl derivatives with fuming nitric acid at room temperature gave 2-methoxy-3-nitro- 4, 5, 6-tribromophenyl acetate and 2-methoxy-3-nitro-4, 5, 6-tribromophenyl m-nitrobenzoate, respectively. It is significant that bromine was not lost in these nitrations and that in the last case both nuclei were nitrated

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