[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.CN(CCN(CCN(C)C)C)C.C([Li])CCC.B(OC)(OC)[O:28]C.OO>O.C(O)(=O)C.C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[OH:28]
To a 200 ml THF solution containing 50.1 g of 1-fluoro-4-methoxybenzene and 70 g of N,N,N′,N′,N″-pentamethyldiethylenetriamine there was added dropwise 150 ml of n-butyllithium (2.66 M, hexane solution) at −74° C. over a period of 30 minutes, under a nitrogen atmosphere. After stirring between −74° C. and −70° C. for 3 hours, 100 ml of trimethyl borate was added. The temperature of the reaction mixture was then slowly raised to room temperature. Next, 70 ml of acetic acid and 75 ml of a 30% hydrogen peroxide aqueous solution were added and the reaction mixture was stirred overnight at room temperature. After the addition of water to the reaction mixture, it was extracted with a hexane/ethyl acetate mixture and dried over anhydrous magnesium sulfate. The desiccant was filtered out, and the filtrate was concentrated under reduced pressure to obtain a crude product of 1-fluoro-2-hydroxy-4-methoxybenzene (65.59 g) as a colorless solid.
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