Chloride → HCID 10670667, compound

Participants

Reaction Steps

12.0 g (25.7 mmol) of (±)-6,6′-dibromo[1,1′]binaphthalinyl-2,2′-diol, 11.5 g (41 mmol) of sodium metaborate octahydrate and 800 mg of bistriphenylphosphinepalladium(II) chloride are initially introduced in 100 ml of water and 20 ml of THF, 0.13 ml of hydrazine hydrate is added, and a solution of 7.0 g (57 mmol) of benzeneboronic acid in 80 ml of THF is added dropwise. The batch is subsequently heated under reflux overnight, added to water and extracted three times with MTB ether. The combined org. phases are washed with water and dried over sodium sulfate. The solvent is removed in vacuo, and the residue is filtered through silica gel with toluene/ethyl acetate (19:1) and evaporated, and the product is recrystallized once each from toluene/cyclohexane (1:1) and isopropanol, giving (±)-6,6′-diphenyl[1,1′]binaphthalinyl-2,2′-diol as colorless crystals.

Provenance & Evidence