Cyclohexanol → 2-[[(4-Chlorophenyl)sulfonyl](cyclohexyl)methyl]-1,4-difluorobenzene

HRID 748691Notes

Reaction equation

HRID 748691 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=2[F:19])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH:20]1(O)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.C(C=P(CCCC)(CCCC)CCCC)#N>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]([CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=2[F:19])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7966Cyclohexanol2×HCID 4622928Cyanomethylenetributylphosphorane2×HCID 99010282-(((4-Chlorophenyl)sulfonyl)methyl)-1,4-difluorobenzene

Product 1

HCID 112576272-[[(4-Chlorophenyl)sulfonyl](cyclohexyl)methyl]-1,4-difluorobenzene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The 2-[(4-chlorophenyl)sulfonylmethyl]-1,4-difluorobenzene (240 mg, 0.793 mmol) obtained in Example 5 was dissolved in toluene (20 ml). To the resulting solution were added cyclohexanol (0.11 ml, 1.0 mmol) and cyanomethylenetri-n-butylphosphorane (250 mg, 1.0 mmol). The resulting mixture was heated under reflux for 14 hours under an argon atmosphere. The reaction mixture was allowed to cool down and then, added with cyclohexanol (0.22 ml, 2.1 mmol) and cyanomethylenetri-n-butylphosphorane (500 mg, 2.08 mmol). The mixture was heated under reflux for 14 hours under an argon atmosphere. After the reaction mixture was allowed to cool down and concentrated under reduced pressure, the residue thus obtained was purified by silica gel chromatography (hexane:ethyl acetate=30:1) to yield a white solid. The resulting white solid was washed with hexane, whereby the title compound (188 mg, 62%) was obtained as a white powder.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 14 hours under an argon atmosphere
  3. temperatureto cool down
  4. temperatureThe mixture was heated
  5. temperatureunder reflux for 14 hours under an argon atmosphere
  6. temperatureto cool down
  7. concentrationconcentrated under reduced pressure
  8. customthe residue thus obtained
  9. customwas purified by silica gel chromatography (hexane:ethyl acetate=30:1)
  10. customto yield a white solid
  11. washThe resulting white solid was washed with hexane, whereby the title compound (188 mg, 62%)
  12. customwas obtained as a white powder

Sources & evidence

ORD record
ord-18b546c1cac44b4496c1bb01b2391806
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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