Dimethylformamide → 3-Bromobenzaldehyde

Participants

Reaction Conditions

Reaction Steps

n-Butylmagnesium chloride (4.00 mmol) in 2.00M tetrahydrofuran solution (2.00 mL) was added to ice-cooled n-butyllithium (8.06 mmol) in 1.55M hexane (5.20 mL). The mixture was stirred at 0° C. for 15 minutes to give a suspension. To the suspension was added dropwise a toluene solution (25 mL) containing 1,3-dibromobenzene (2.36 g, 10.0 mmol), while keeping the temperature below 5° C., over a period of 15 minutes, thereby to give a suspension. The suspension was stirred at 0° C. for 5 hours, and then N,N-dimethylformamide (1.0 mL, 13 mmol) was added thereto. The resultant mixture was stirred at 0° C. for 30 minutes, and 10% aqueous acetic acid (20 mL) was added. The reaction mixture was extracted twice with toluene (20 mL). The organic extracts were combined, washed with water (20 mL), and dried over magnesium sulfate. Toluene was added to the solution to a volume of 85 mL. The solution (83 ml) was purified by flash column chromatography on silica gel in a developing solvent system of hexane-ethyl acetate (25:1, v/v) to give the title compound (1.446 g, 78% yield) as a pale yellowish crystalline solid.

Provenance & Evidence