Dimethylformamide → 4-Bromobenzaldehyde

Temperature

0 °C

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 1,4-dibromobenzene (2.36 g, 10 mmol) over a period of 15 minutes, while keeping the temperature below 5° C., to give a white suspension. After the suspension was stirred at 0° C. for 5 hours, N,N-dimethylformamide (1.0 mL, 13 mmol) was added thereto. The resultant mixture was stirred at 0° C. for 30 minutes, and 10% acetic acid solution (20 mL) was added. The organic phase was separated and the aqueous phase was extracted with toluene (20 mL). The organic layers were combined, washed with water (20 mL), and dried over magnesium sulfate. Toluene was added to the solution to a volume of 100 mL. The solution (98 ml) was purified by flash column chromatography on silica gel in a developing solvent system of hexane-ethyl acetate (30:1, v/v) to give the title compound (1.507 g, 81% yield) as a colorless crystalline solid.

1. customto give a suspension
2. customthe temperature below 5° C.
3. customto give a white suspension
4. stirringAfter the suspension was stirred at 0° C. for 5 hours
5. customThe organic phase was separated
6. extractionthe aqueous phase was extracted with toluene (20 mL)
7. washwashed with water (20 mL)
8. dry with materialdried over magnesium sulfate
9. additionToluene was added to the solution to a volume of 100 mL
10. customThe solution (98 ml) was purified by flash column chromatography on silica gel in a developing solvent system of hexane-ethyl acetate (30:1

ORD record

ord-bb2fa6b60fea4c82af7675d3d7700569

Source dataset

uspto-grants-2008_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07439535B2