Dimethylformamide → p-Cyclohexylbenzaldehyde

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To a solution of 1-bromo-4-cyclohexylbenzene (850 mg, 3.55 mmol) in THF (4.0 mL) was added n-BuLi (3.1 mL, 4.62 mmol) at −78° C. under an inert atmosphere. The reaction mixture was stirred for 60 min at −78° C., and then DMF (2.8 mL) was added. The reaction mixture was then stirred for an additional hour at −78° C., warmed to 0° C., and quenched with a saturated NH4Cl solution. The mixture was then extracted with ethyl acetate (2×30 mL). The combined organic layers were then dried over magnesium sulfate, filtered and concentrated in vacuo to obtain the crude product. The crude material was purified via silica gel column chromatography to afford 4-cyclohexylbenzaldehyde (250 mg, 38%) as a solid.

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