2-Hydroxy-5-(trifluoromethoxy)benzaldehyde → 2-(1-Phenylthiocycloprop-1-yl)oxy-5-(trifluoromethoxy)benzaldehyde

Participants

Reaction Conditions

Reaction Steps

Silver carbonate (1.2 g, 4.34 mmol) was added to a solution of 2-hydroxy-5-(trifluoromethoxy)benzaldehyde (0.5 g, 2.43 mmol) and (1-iodocycloprop-1-yl)phenylsulfide (Cohen T. and Matz J. R., J. Am. Chem. Soc. 1980, 102, 6902) (1.2 g, 4.34 mmol) in toluene (30 mL) and the mixture was stirred at 40° C. overnight. The mixture was cooled, diluted with ethyl acetate and filtered, washing well with ethyl acetate. The mixture was washed with aqueous sodium hydroxide, dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with hexane/Et2O (95:5), to give the title compound as a yellow oil (191 mg, 27%). 1H NMR (360 MHz, CDCl3) δ1.51-1.56 (2 H, m), 1.44-1.48 (2 H, m), 7.25-7.35 (7 H, m), 7.69 (1 H, d, J 2.0 Hz), and 10.26 (1 H, s).

Provenance & Evidence