Hexane → 2-[1-[(4-Chlorophenyl)sulfonyl]-5-(methylthio)pentyl]-1,4-difluorobenzene

HRID 748682Notes

Reaction equation

HRID 748682 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][S:21][CH2:22][CH2:23][CH2:24][CH2:25]O.C(C=P(CCCC)(CCCC)CCCC)#N.CCCCCC>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])[CH2:25][CH2:24][CH2:23][CH2:22][S:21][CH3:20])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 5197934-(Methylthio)butanol2×HCID 4622928CyanomethylenetributylphosphoraneHCID 99010282-(((4-Chlorophenyl)sulfonyl)methyl)-1,4-difluorobenzene

Product 1

HCID 597509322-[1-[(4-Chlorophenyl)sulfonyl]-5-(methylthio)pentyl]-1,4-difluorobenzeneYield 64.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The 2-[(4-chlorophenyl)sulfonylmethyl]-1,4-difluorobenzene (0.94 g, 3.1 mmol) obtained in Example 5 was dissolved in toluene (15 ml). After addition of 4-(methylthio)-1-butanol (0.25 ml, 2.1 mmol) and cyanomethylenetri-n-butylphosphorane (1.0 g, 4.1 mmol), the resulting mixture was heated under reflux for 14 hours under an argon atmosphere. The reaction mixture was allowed to cool down. Then, 4-(methylthio)-1-butanol (0.25 ml, 2.1 mmol) was added, followed by heating under reflux for 6 hours under an argon atmosphere. The reaction mixture was allowed to cool down and then, concentrated under reduced pressure. The residue thus obtained was purified by silica gel chromatography (hexane:ethyl acetate=10:1) to yield a colorless oil. The resulting colorless oil was solidified with hexane, whereby the title compound (0.55 g, 44%) 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. temperatureby heating
  5. temperatureunder reflux for 6 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=10:1)
  10. customto yield a colorless oil

Sources & evidence

ORD record
ord-eb6a26dc5e1d45e590abc446b456e83b
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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