Cyclohexanone → 2-[4-(trifluoromethyl)phenyl]cyclohexan-1-one

HRID 406333Notes

Reaction equation

HRID 406333 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=1.[C:12]1(=[O:18])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.CC(C)([O-])C.[K+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2N(C)C)CCCCC1>O1CCCC1.COC(C)(C)C>[F:9][C:8]([F:11])([F:10])[C:5]1[CH:6]=[CH:7][C:2]([CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17][C:12]2=[O:18])=[CH:3][CH:4]=1

Participants

7

Reactant 4

HCID 7967CyclohexanoneHCID 67872Benzene, 1-bromo-4-(trifluoromethyl)-HCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 23665647Potassium tert-butoxide

Product 1

HCID 113110452-[4-(trifluoromethyl)phenyl]cyclohexan-1-one

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
70 °C

Procedure

1-Bromo-4-trifluoromethylbenzene (5 mL), cyclohexanone (7.4 mL) and potassium tert-butoxide (8 g) were suspended in tetrahydrofuran (100 mL). Tris(dibenzylieneacetone)dipalladium (1.3 g) and 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl (843 mg) were added and the mixture was heated with stirring at 70° C. in a nitrogen atmosphere for 1.5 hours. After leaving to cool, tert-butyl methyl ether was added, followed by filtration through celite. The resulting organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography three times. The resulting solid was washed with heptane to obtain the title compound (2.1 g). The property values of the compound are as follows.

Workup

  1. temperaturethe mixture was heated
  2. customAfter leaving
  3. temperatureto cool
  4. filtrationfollowed by filtration through celite
  5. concentrationThe resulting organic layer was concentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography three times
  7. washThe resulting solid was washed with heptane

Sources & evidence

ORD record
ord-19f20883b9a645e7a944d0cd86ec67a8
Source dataset
uspto-grants-2014_06
Patent number
US08754100B2

Reaction notes

Loading…