5-Bromosalicylaldehyde → HCID 23508725, compound

Participants

Reaction Steps

0.6 g of bis(dibenzylideneacetone)palladium and 0.16 g of tri-tert-butylphosphine are added under nitrogen to 200 ml of toluene, and the resultant dark-red solution is stirred at 20° for 20 minutes. 10 g of 5-bromo-2-hydroxybenzaldehyde, 9.7 g of 1-benzylpiperazine and 7.2 g of sodium tert-butoxide are then added. The mixture is stirred at 60° for 24 hours and cooled, 800 ml of water are added, and the mixture is extracted with 2×500 ml of ethyl acetate. The organic phases are combined and washed with 300 ml of water, and the solvent is removed at 30° under reduced pressure. The dark-orange oil which remains (9.7 g) is purified by chromatography (300 g of silica gel; MTB ether/heptane 5:1; 1.5 litres). 9.9 g of pale-yellow crystals remain (67%), m.p. 101-103°; MS 296 (M+), 205, 119, 91 (100%).

Provenance & Evidence