Iodine → HCID 21281111, compound

Participants

Reaction Steps

Magnesium turnings (2.4 g, 100 mmol) were activated with a crystal of iodine by heating under nitrogen the cooled magnesium and 6.1 g of 1-bromopentane (40 mmol, 99% purity) in 200 mL of ether. The reaction medium was heated to reflux and the reaction was self-sustaining. After 0.75 h the reaction was complete and the mixture was cooled to ice bath temperatures and 5 g of 1-(3-phenoxyphenyl)-pyrrole-2-aldehyde (19 mmol) in 25 mL of ether was added. The reaction was stirred for 1 h and poured into 500 ml of 1N NH4Cl solution. The product was extracted into ether and the ether was cross washed with 1 N NH4Cl solution. The etherate was separated, dried with MgSO4 and filtered, and the solvent was evaporated, yielding 6.35 g of crude product. The product was column chromatographed three times on silica gel (for dry column chromatography) and finally on Florisil eluting with ether acetate/hexane (1:40, v/v). After solvent removal, there was obtained 1.1 g of the final product. The product gave correct elemental analysis and spectral identification.

Provenance & Evidence