4-Bromo-2-fluorobenzaldehyde → 2-(4-Bromo-2-fluorophenyl)vinyl methyl ether

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Reaction Steps

Methoxymethyl)triphenylphosphonium chloride (147 g, 0.48 mol) was suspended in tetrahydrofuran (1.5 L) under an argon atmosphere, and cooled to 0° C. t-BuOK (51.6 g, 0.46 mol) was added in portions. A solution of 4-bromo-2-fluorobenzaldehyde (40.6 g, 0.2 mol) in tetrahydrofuran (500 mL) was then added to the reaction mixture. The solution was stirred at room temperature for 1 hour. The solution was poured into ice-water and extracted with ethyl acetate (2×). The combined organic phases were dried and concentrated in vacuo. Purification via flash chromatography afforded the title compound.

Provenance & Evidence