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

HRID 2080374Notes

Reaction equation

HRID 2080374 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-difluorobenzeneYield 62%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 14 hours under an argon atmosphere
  3. temperatureto cool
  4. temperatureUnder an argon atmosphere, the resulting mixture was heated
  5. temperatureunder reflux for 14 hours
  6. temperatureto cool
  7. concentrationconcentrated under reduced pressure
  8. customThe residue thus obtained
  9. customwas purified by silica gel chromatography (hexane:ethyl acetate=30:1)
  10. customto give a white solid
  11. washThe white solid was washed with hexane

Sources & evidence

ORD record
ord-1c2cf0daba3b4341916c2614462c2764
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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