Carbofuran → 2,3-Dihydro-2,2-dimethyl-7-nitrobenzofuran

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Reaction Steps

Carbofuran is a commercially available material. It is manufactured by the simultaneous thermal rearrangement and cyclization of 1-methallyloxy-2-nitrobenzene to form 2,3-dihydro-2,2-dimethyl-7-nitrobenzofuran, which is then reduced to the amine, then diazotized and converted to 2,3-dihydro-2,2-dimethylbenzofuran-7-ol, and then esterified with methyl isocyanate. In an alternative procedure, 2-methallyloxyphenol is thermally rearranged and cyclized to form 2,3-dihydro-2,2-dimethylbenzofuran-7-ol, which is then treated simultaneously with methyl isocyanate and triethylamine. The starting material 2-methallyloxyphenol can be prepared by reacting catechol with potassium carbonate and potassium iodide in dry acetone under a nitrogen atmosphere. Further particulars of each of these procedures will be readily apparent to those skilled in the art.

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