4-Bromotoluene → 2-(4-Methylphenyl)cyclohexanone

Temperature

-20 °C

To a solution of p-tolylbromide (17.1 g, 100 mmol) in dry THF (100 mL) was added magnesium (2.43 g, 100 mmol) and then the resulting mixture was cooled to −20° C. and (CuBr-dimethylsulfide complex (2.0 g, 10 mmol) was added and the mixture stirred at −20° C. for 10 min. Then a solution of cyclohexene oxide (10 mL, 100 mmol) in dry THF (10 mL) was added dropwise and the reaction warmed to 0° C. at which point an exothermic reaction initiates. With ice-bath cooling the temperature can be maintained below 25° C. The reaction mixture was then stirred at 0–5° C. for an additional 2 h, then quenched with ammonium chloride solution (saturated, 30 mL) and the product extracted with tert-butyl methyl ether. The combined organic extracts were then washed with water, dried over sodium sulfate, filtered and evaporated. Recrystallisation from hexane afforded the title compound (9.9 g, 52%) as white crystals. MS: m/e=190.1 (M).

1. addition(CuBr-dimethylsulfide complex (2.0 g, 10 mmol) was added
2. temperaturethe reaction warmed to 0° C. at which point
3. customan exothermic reaction initiates
4. temperatureWith ice-bath cooling the temperature
5. temperaturecan be maintained below 25° C
6. stirringThe reaction mixture was then stirred at 0–5° C. for an additional 2 h
7. customquenched with ammonium chloride solution (saturated, 30 mL)
8. extractionthe product extracted with tert-butyl methyl ether
9. washThe combined organic extracts were then washed with water
10. dry with materialdried over sodium sulfate
11. filtrationfiltered
12. customevaporated
13. customRecrystallisation from hexane

ORD record

ord-dbdc012434d14b29ad26b2a4c8b33917

Source dataset

uspto-grants-2007_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07173133B2