Hydrochloric Acid → 5-Bromo[1,1'-biphenyl]-3-ol

Participants

Reaction Conditions

Reaction Steps

Toluene (400 mL) and water (20 mL) were added to a mixture of 3-,5-dibromophenol (5.088 g, 19.85 mmol), phenylboronic acid (2.42 g, 19.85 mmol) and potassium carbonate (5.48 g, 39.7 mmol) in a round bottom flask. This was followed by addition of 1.149 g of tetrakis(triphenylphosphine)palladium(0) under a atmosphere of nitrogen. This mixture was stirred at heated overnight at 90° C. At this time, HCl (2 N aq) was added to the reaction mixture until pH=˜2 and the subsequent two phases were separated; the aqueous phase was extracted and washed three time with ethyl acetate. The combined organic phases were dried with MgSO4, filtered and washed with ethyl acetate. The filtrate was concentrated in vacuo to provide an orange oil. Analysis of the oil by LC/MS indicated a mixture of desired product, starting material and the bis-phenyl coupling product The mixture was carried on to the next aryl boronic acid coupling step 2.

Provenance & Evidence