3-Allyl-2',6'-dichloro-biphenyl-2-ol → 2',6'-dichloro-3-[(1E)-prop-1-enyl]-1,1'-biphenyl-2-ol

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Reaction Steps

A mixture of 3-allyl-2′,6′-dichloro-1,1′-biphenyl-2-ol (2.922 g, 10.47 mmol) and bis(acetonitrile)dichloropalladium (II) (136 mg, 0.523 mmol) in anhydrous dichloromethane was heated to reflux under nitrogen for 1 hour. The cooled reaction mixture was then concentrated to a small volume under reduced pressure and directly pre-adsorbed onto silica gel. Purification by flash chromatography using a solvent gradient of 2 to 7.5% ethyl acetate in hexane gave 2.81 g (96%) of 2′,6′-dichloro-3-[(1E)-prop-1-enyl]-1,1′-biphenyl-2-ol as a colorless syrup. HRMS: calcd for C15H12Cl2O, 278.02652. found (EI, M+), 278.0262.

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