2-Methyl-2-butene → 3-Cyano-4-fluorobenzoic acid

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Reaction Steps

Sodium chlorite (1.819 g, 20.12 mmol) and potassium dihydrogen phosphate (0.228 g, 1.676 mmol) in water (20.00 ml) was added to 2-fluoro-5-formylbenzonitrile (Aldrich; 1 g, 6.71 mmol) in t-butanol (20 ml), followed by 2-methyl-2-butene (10.06 ml, 20.12 mmol). The resulting mixture was stirred at room temperature for 2 hrs. A solution of 4.5 g of sodium disulfite in water (100 ml) was then added carefully. DCM (150 ml) was added and phases were separated. The aqueous layer was then extracted once more with DCM (150 ml). The combined organic extracts were passed through a phase separation cartridge, concentrated under vacuum and dried in a vacuum oven to give the title compound as a white solid (1.09 g).

Provenance & Evidence