2-Methyl-2-butene → 3-Cyano-4-(2,2,2-trifluoroethoxy)benzoic acid

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Reaction Steps

5-formyl-2-[(2,2,2-trifluoroethyl)oxy]benzonitrile (D29; 155 mg, 0.676 mmol) was dissolved in t-butanol (2 ml). A solution of potassium dihydrogen phosphate (23.01 mg, 0.169 mmol) and sodium chlorite (184 mg, 2.029 mmol) in water (2 ml) was added, followed by 2-methyl-2-butene (1.015 ml, 2.029 mmol). The resulting mixture was stirred at room temperature for 4 hrs. A solution of sodium disulfite (450 mg) in water (10 ml) was added carefully. DCM (15 ml) was then added and the phases were separated. The aqueous layer was then extracted once more with DCM (15 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 (173 mg).

Provenance & Evidence