Hydrogen Peroxide → 2,3-Difluoro-4-hydroxy-4'-octyloxybiphenyl

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A solution of n-butyllithium (1.60 ml, 10.0 M in hexanes, 0.016 mol) was added dropwise to a stirred, cooled (−78° C.) solution of 2,3-difluoro-4′-octyloxybiphenyl [see M. Hird and K. L. Toyne, J. Mater. Chem., 1995, 5, 2239] (4.70 g, 0.015 mol) in dry THF (250 ml) under dry nitrogen. The mixture was stirred at −78° C. for 2 hr and a solution of trimethyl borate (3.15 g, 0.030 mol) in dry THF (10 ml) was added. The mixture was allowed to warm to room temperature overnight and a solution of 30% hydrogen peroxide (50 ml) in acetic acid (500 ml) was added dropwise at room temperature. The mixture was extracted into ether (3 times) and the combined ethereal extracts were washed with water and dried over MgSO4. The solvent was removed in vacuo and the residue was recrystallised from ethanol to yield colourless crystals (3.45 g, 69%), mp 145° C.

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