m-Chloroperbenzoic acid → 2-(4-Chlorophenyl)cyclobutanone

Temperature

0 °C

To a solution of 1-chloro-4-(cyclopropylidenemethyl)benzene (5 g, 30 mmol) in CH2Cl2 (80 ml) was added in 5 separate portions m-chloroperbenzoic acid (5.3 g, 30 mmol) at 0° C. After stirring at 0° C. for 3 h, the reaction mixture was washed with saturated NaHCO3 aqueous solution and brine, dried over Na2SO4 and concentrated. To the crude product in CH2Cl2 (40 ml) was added 10% HBF4 (11.6 ml 48% HBF4 and 46 ml H2O). After stirring at rt for 17 h, the mixture was extracted with CH2Cl2, washed with saturated NaHCO3 aq. solution and brine. The solvent was removed in vacuo, and the residue was purified by column chromatography on silica gel (eluent i-hexane, KMnO4 stain) to give 2-(4-chlorophenyl)cyclobutanone (3.470 g, 64%).

1. washthe reaction mixture was washed with saturated NaHCO3 aqueous solution and brine
2. dry with materialdried over Na2SO4
3. concentrationconcentrated
4. additionTo the crude product in CH2Cl2 (40 ml) was added 10% HBF4 (11.6 ml 48% HBF4 and 46 ml H2O)
5. stirringAfter stirring at rt for 17 h
6. extractionthe mixture was extracted with CH2Cl2
7. washwashed with saturated NaHCO3 aq. solution and brine
8. customThe solvent was removed in vacuo
9. customthe residue was purified by column chromatography on silica gel (eluent i-hexane, KMnO4 stain)

ORD record

ord-28cd39344d7143d59e3fc0c3b1991738

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09414589B2