Hydrochloric Acid → HCID 68109197, compound

Participants

Reaction Steps

17.2 g (69.0 mmol) of 4-bromo-4′-hydroxybiphenyl, 10.0 g (143 mmol) of but-3-yn-1-ol, 2.00 g (2.85 mmol) of bis(triphenylphosphine)palladium(II) chloride, 0.7 g of copper(I) iodide and 25 ml (178 mmol) of diisopropylamine are heated under reflux overnight in 150 ml of THF. The batch is subsequently added to 200 ml of MTB ether, 400 ml of water are added, and the mixture is acidified using hydrochloric acid. The aqueous phase is separated off and extracted three times with ethyl acetate. The combined org. phases are evaporated in vacuo, and the residue is filtered through silica gel with dichloromethane/ethyl acetate (3:1). Crystallisation of the crude product from toluene gives 4′-(4-hydroxybut-1-ynyl)biphenyl-4-ol as a colourless solid.

Provenance & Evidence