p-Toluenesulfonic acid → 1-(Difluoro-phenyl)-4-(p-propylphenyl)-cyclohex-1-ene

HRID 327373Notes

Reaction equation

HRID 327373 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[F:8].C([Li])CCC.[CH2:14]([C:17]1[CH:22]=[CH:21][C:20]([CH:23]2[CH2:28][CH2:27][C:26](=O)[CH2:25][CH2:24]2)=[CH:19][CH:18]=1)[CH2:15][CH3:16].CC1C=CC(S(O)(=O)=O)=CC=1>C1COCC1.CCCCCC>[F:1][C:2]1[C:3]([F:8])=[C:4]([C:26]2[CH2:27][CH2:28][CH:23]([C:20]3[CH:19]=[CH:18][C:17]([CH2:14][CH2:15][CH3:16])=[CH:22][CH:21]=3)[CH2:24][CH:25]=2)[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 97061,2-DifluorobenzeneHCID 144957544-(4-Propylphenyl)cyclohexan-1-oneHCID 178418339Butyllithium

Product 1

HCID 144957551-(Difluoro-phenyl)-4-(p-propylphenyl)-cyclohex-1-ene

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

To a mixture of 1,2-difluorobenzene (0.1 mol) and 100 ml THF a mixture of n-butyllithium (0.105 ml) and 60 ml hexane is added at -70° C. After stirring for 6 h a mixture of 4-(p-propylphenyl)-cyclohexanone (0.1 mol) and 50 ml THF is added. After stirring for 2 h, warming to room temperatures, boiling with PTSA as described for 10A and usual work-up 1-(difluoro-phenyl)-4-(p-propylphenyl)-cyclohex-1-ene is obtained.

Workup

  1. additionis added at -70° C
  2. additionis added
  3. stirringAfter stirring for 2 h
  4. temperaturewarming to room temperatures

Sources & evidence

ORD record
ord-e9d051bfb0a749899c6bce1c3096fc52
Source dataset
uspto-grants-1993_12
Patent number
US05273680

Reaction notes

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