Aminoammonium hydroxide → HCID 58471579, compound

Participants

Reaction Steps

A mixture of 4.55 g (18.4 mmol) of 4-butoxy-2-fluorobromobenzene, 9.10 g (15.7 mmol) of 2-{4-[difluoro-(2,3′,5′-trifluoro-4′-trifluoromethylbiphenyl-4-yloxy)methyl]-3,5-difluorophenyl}-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 0.36 g (0.50 mmol) of bis(triphenylphosphine)palladium(II) chloride and 3.35 g (12.0 mmol) of sodium metaborate octahydrate is initially introduced in 60 ml of THF/water=4:1. 0.024 ml (0.5 mmol) of hydrazinium hydroxide is added, and the mixture is refluxed for 19 h. After cooling, the batch is diluted with MTBE, and the mixture is washed with water. The organic phase is separated off, and the aqueous phase is extracted with MTBE. The combined organic phases are washed with water. The solution is dried using sodium sulfate and concentrated to dryness. The residue is purified by column chromatography (SiO2, n-heptane:toluene=9:1→3:1). The further purification is carried out by recrystallisation from ethanol and n-heptane, giving 4-[difluoro(3,5,2′-trifluoro-4′-butoxybiphenyl-4-yl)methoxy]-6,3′,5′-trifluoro-4′-trifluoromethylbiphenyl as a colourless solid.

Provenance & Evidence