Hydroxylamine → 2,3-Difluoro-6-(trifluoromethyl)benzamide

Beteiligte Stoffe

Reaktionsschritte

In a colorless, transparent glass reaction vessel was placed a mixed solvent of 150 ml of methanol-distilled water (volume ratio 1:2) into which were dissolved beforehand 9.91 g (150 mmol) of 50% hydroxylamine aqueous solution, 99 mg (0.50 mmol) of o-phenanthroline and on purpose 86 μg (0.00068 mmol) of iron(II) chloride. Into the mixed solvent was added 10.36 g (50.0 mmol) of 2,3-difluoro-6-trifluoromethylbenzonitrile (I″). The reaction temperature stood at 60° C. for 6 hours and was returned to room temperature. When the reaction solution was analyzed with HPLC [column: Inertsil ODS—34.6 mm ø×250 mm (GL Sciences Inc.), mobile phase; CH3CN—H2O—10% H3PO4 500:500:10 (v/v/v), flow rate; 1.0 ml/min, detection wavelength; 225 nm, and the same conditions for Example 2 and after], it was shown that (I″) (tR 16.0 min) disappeared, 2,3-difluoro-6-trifluoromethylbenzamidoxime (II′) was mainly produced (yield 76.9%, tR 3.6 min) and 2,3-difluoro6-trifluoromethylbenzamide (III′) was produced as a byproduct (yield 8.4%, tR 4.8 min).

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