2,6-Lutidine → 3,5-Difluoro-4-triisopropylsilanyloxybenzaldehyde

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Reaction Steps

30.0 g (190 mmol) of 3,5-difluoro-4-hydroxybenzaldehyde [CAS 118276-06-5] are dissolved under argon in 600 ml of dichloromethane and, at 0° C., 44.7 g (417 mmol) of 2,6-lutidine are added. Then 87.2 g (284 mmol) of triisopropylsilyl trifluoromethanesulfonate are added dropwise, and the mixture is stirred at RT for 12 h. The solvent is distilled out in vacuo, and the residue is mixed with ammonium chloride solution and stirred for 5 min, and the organic phase is separated off. A further extraction with dichloromethane is carried out, and the organic phases are combined, washed with saturated sodium chloride solution, dried over magnesium sulfate, filtered and washed with dichloromethane, and the solvent is distilled off in vacuo. Chromatography on silica gel 60 (mobile phase: cyclohexane) results in 34.9 g (111 mmol, 58% of theory) of the title compound.

Provenance & Evidence