Hydrochloric Acid → HCID 118362025, compound

Participants

Reaction Steps

11.0 g (41.6 mmol) 2-[4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolane-2-yl)phenoxy]-ethanol, 5.25 g (20.8 mmol) 3,5-Dibromophenol and 34.4 g (125 mmol) sodium metaborate-tetrahydrate are suspended in 60 ml THF and 60 ml water and 1.36 g (2 mmol) palladium(dppf) are added. The mixture is heated overnight at reflux. After addition of 100 ml water and 100 ml MTB ether the mixture is acidified with 2M hydrochloric acid. The organic layer is separated and the aqueous layer is extracted three times with MTB ether. The combined organic layers are dried over sodium sulfate and the solvent is removed in vacuo. The crude product is filtered through silica gel with toluene/ethyl acetate (1:1 to 0:1) to yield a yellow oil, which crystallizes from dichloromethane.

Provenance & Evidence