3-Hexanol → 2-[1-[(4-Chlorophenyl)sulfonyl]-2-ethylpentyl]-1,4-difluorobenzene

HRID 748827Notes

Reaction equation

HRID 748827 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.[CH3:20][CH2:21][CH:22](O)[CH2:23][CH2:24][CH3:25].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]([C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=2[F:19])[CH:22]([CH2:21][CH3:20])[CH2:23][CH2:24][CH3:25])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 121783-HexanolHCID 4622928CyanomethylenetributylphosphoraneHCID 99010282-(((4-Chlorophenyl)sulfonyl)methyl)-1,4-difluorobenzene

Product 1

HCID 597507412-[1-[(4-Chlorophenyl)sulfonyl]-2-ethylpentyl]-1,4-difluorobenzene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The 2-[(4-chlorophenyl)sulfonylmethyl]-1,4-difluorobenzene (200 mg, 0.661 mmol) obtained in Example 5 and 3-hexanol (0.150 ml, 1.35 mmol) were dissolved in toluene (3 ml), followed by the addition of cyanomethylenetri-n-butylphosphorane (0.320 ml). Under an argon atmosphere, the resulting mixture was heated under reflux for 14 hours. The reaction mixture was then allowed to cool down. The residue obtained by concentrating the reaction mixture under reduced pressure was separated and purified by flash silica gel chromatography (hexane:ethyl acetate=200:1), whereby obtained were the title Isomer 293-A (low polarity) (37 mg, 0.096 mmol, 15%) and the title Isomer mixture (44 mg, 0.11 mmol, 17%), each as a white powder.

Workup

  1. temperatureUnder an argon atmosphere, the resulting mixture was heated
  2. temperatureunder reflux for 14 hours
  3. temperatureto cool down
  4. customThe residue obtained
  5. concentrationby concentrating the reaction mixture under reduced pressure
  6. customwas separated
  7. custompurified by flash silica gel chromatography (hexane:ethyl acetate=200:1), whereby
  8. customobtained

Sources & evidence

ORD record
ord-69a10fca3f4c4b6f923442ab690c8fd3
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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