Triacetoxyperiodinane → 3-Fluoro-4-formylbenzonitrile

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Reaction Steps

A solution of Example 53B (340 mg, 2.25 mmol) in dichloromethane (10 mL) at room temperature was treated with Dess-Martin periodinane (1.9 g, 4.5 mmol), stirred for 5 minutes, and concentrated. The concentrate was dissolved in ethyl acetate, washed with saturated sodium bicarbonate, dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 10:1 hexanes/ethyl acetate to provide the desired product. 1H NMR (500 MHz, CDCl3) δ 10.42 (s, 1H), 8.01 (dd, 1H), 7.62-7.58 (m, 1H), 7.54 (dd, 1H);

Provenance & Evidence