Phosphorus trichloride → 2',5-Dichloro-1,6-dihydro[1,1'-biphenyl]-3(2H)-one

Temperature

100 °C

To a solution of 5-(2-chlorophenyl)cyclohexane-1,3-dione (3.0 g) in chloroform(10 ml) was added phosphorus trichloride (0.62 g), and the mixture was stirred at 100° C. for 2.5 hours. To the mixture was added phosphorus trichloride (0.62 g), and the mixture was stirred at 100° C. for 2 hours. The reaction solution was concentrated under reduced pressure, and to the residue was added ice-water. The mixture was extracted with ethyl acetate, and the organic layer was washed with water and saturated brine, dried with magnesium sulfate and concentrated under reduced pressure to give 3-chloro-5-(2-chlorophenyl)-2-cyclohexen-1-one, which was dissolved in ethanol (3 ml). To the solution were added sodium sulfide 9 hydrate (2.0 g) and water (3 ml), and the mixture was stirred at room temperature for 2 hours and concentrated under reduced pressure. The residue was dissolved in water, and the solution was washed with diethylether. To the aqueous layer was added 4N hydrochloric acid to make the solution acidic, and the solution was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried with magnesium sulfate and concentrated under reduced pressure to give oil of 5-(2-chlorophenyl)-3-mercapto-2-cyclohexen-1-one (1.8 g).

1. stirringthe mixture was stirred at 100° C. for 2 hours
2. concentrationThe reaction solution was concentrated under reduced pressure
3. additionto the residue was added ice-water
4. extractionThe mixture was extracted with ethyl acetate
5. washthe organic layer was washed with water and saturated brine
6. dry with materialdried with magnesium sulfate
7. concentrationconcentrated under reduced pressure

ORD record

ord-cb67c95dea8f4de6b2bdd38e795dc811

Source dataset

uspto-grants-2002_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06350749B1