Dimethylformamide → 2-Cyclopropoxy-5-(trifluoromethoxy)benzaldehyde

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Reaction Conditions

Reaction Steps

1-(Cyclopropoxy)-2-iodo-4-(trifluoromethoxy)benzene (Description 12; 5.84 g, 17 mmol) was dissolved in tetrahydrofuran (150 mL) and cooled to −78° C. Tert-butyl lithium solution (20 mL, 1.7M in pentanes, 34 mmol) was then added dropwise. The solution was stirred at −78° C. for 10 minutes, before N,N′-dimethylformamide (5.3 mL, 68 mmol) was added, and the resulting solution allowed to stir to room temperature. Saturated aqueous ammonium chloride solution (50 mL) was then added and the mixture extracted with diethyl ether (2×100 mL). The extracts were dried (MgSO4) and concentrated to yield an oil. Purification of this by silica chromatography gave the title compound as a clear oil (3.94 g, 16 mmol).

Provenance & Evidence