2-Fluoro-4-(hydroxymethyl)benzonitrile → 2-Fluoro-4-formylbenzonitrile

Participants

Reaction Conditions

Reaction Steps

A solution of Example 52B (1.23 g, 8.17 mmol) in 1,4-dioxane (30 mL) was treated with MnO2, heated to 100° C. for 1 hour, and cooled to room temperature. The cooled solution was filtered through diatomaceous earth (Celite®) on a fritted funnel rinsing with 1:1 dichloromethane/methanol (200 mL). The filtrate was concentrated and the concentrate was purified by flash column chromatography on silica gel with a solvent gradient of 19:1 to 4:1 hexanes/ethyl acetate to provide the desired product. MS (APCI) m/z 149 (M+H)+; 1H NMR (300 MHz, CDCl3) δ 10.06 (s, 1H), 7.88-7.71 (m, 3H).

Provenance & Evidence