Dimethylformamide → HCID 118113146, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 4-bromobenzaldehyde (2.00 g), bis(triphenylphosphine)palladium(II) dichloride (228 mg), copper(I) iodide (20.6 mg), N,N-dimethylformamide (2.00 mL) and triethylamine (15.1 mL), cyclopropylacetylene was added and thereafter the mixture was stirred in a sealed tube at 110° C. for one minute under irradiation with microwaves. After being cooled to room temperature, the reaction mixture was poured into a saturated aqueous solution of ammonium chloride and extracted with a liquid mixture of n-hexane/ethyl acetate (1:1) three times. The combined organic layers were washed with saturated brine and dried over added anhydrous magnesium sulfate. The desiccant was removed by filtration and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=100:0-60:40) to give 4-(cyclopropylethynyl)benzaldehyde as a brown oil (1.79 g).

Provenance & Evidence