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sodium nitrite in acetic acid 48 h; Yield given;

1: 85 percent / imidazole / dimethylformamide / Ambient temperature 2: 0.029 g / (dimethylamido)pyridine / dimethylformamide; acetonitrile / 1.5 h / Ambient temperature 3: 71 percent / 2,2'-azobis(2-methylpropionitrile), tributyltin hydride / toluene / 0.5 h / Heating 4: 78 percent / 1 M tetrabutylammonium fluoride / tetrahydrofuran / 0.18 h / Ambient temperature View Scheme