Chlorobenzene → Undecane

Chlorobenzene (45.0 mg, 0.4 mmol) and a THF solution of p-tolylmagnesium bromide (0.98 mL, 1.02 M, 1.0 mmol) was added to CoF2.4H2O (3.38 mg, 0.02 mmol), and 1,3-bis(2,6-diisopropylphenyl)imidazolinium chloride (25.6 mg, 0.06 mmol) at 0° C. under argon atmosphere. The mixture was reacted at 60° C. for 24 hours. After cooled to the ambient temperature, 1.0 mL of saturated sodium potassium tartrate aqueous solution was added to the reaction mixture. The water layer was extracted five times using Et2O. The total organic extract was filtrated by Florisil pad (100-200 mesh, Nacalai Tesque, Inc.). As the internal standard, gas chromatographic analysis was performed using undecane (42.2 μL, 0.2 mmol) (yield=91%). After removing the solvent under reduced pressure, the crude product was purified by silica gel chromatography (pentane), thereby obtaining the above compound, which was a colorless liquid (0.059 g, yield=88%, purity=>99% (GC analysis)).

1. customThe mixture was reacted at 60° C. for 24 hours
2. additionwas added to the reaction mixture
3. extractionThe water layer was extracted five times
4. extractionThe total organic extract
5. filtrationwas filtrated by Florisil pad (100-200 mesh, Nacalai Tesque, Inc.)

ORD record

ord-cf6ccc310f674338801161aea25da523

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08211820B2