1-Phenylethanol → 2-[1-(4-Chlorophenylsulfonyl)-2-phenylpropyl]-1,4-difluorobenzene

HRID 748830Notes

Reaction equation

HRID 748830 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.[C:20]1([CH:26](O)[CH3:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH: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]([C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=2[F:19])[CH:26]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH3:27])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 74091-PhenylethanolHCID 4622928CyanomethylenetributylphosphoraneHCID 99010282-(((4-Chlorophenyl)sulfonyl)methyl)-1,4-difluorobenzene

Product 1

HCID 597507402-[1-(4-Chlorophenylsulfonyl)-2-phenylpropyl]-1,4-difluorobenzene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Under an argon atmosphere, the 2-[(4-chlorophenyl)sulfonylmethyl]-1,4-difluorobenzene (100 mg, 0.330 mmol) obtained in Example 5, and DL-1-phenylethyl alcohol (79.9 μl, 0.661 mmol) were dissolved in toluene (3 ml), followed by the addition of cyanomethylenetri-n-butylphosphorane (159 μl, 0.661 mmol). The resulting mixture was heated under reflux for 13 hours under an argon atmosphere. The reaction mixture was then concentrated. The residue thus obtained was separated and purified by flash chromatography on a silica gel column (hexane:ethyl acetate=85:15). The solids thus obtained were each washed with hexane, whereby obtained were the title Isomer 299-A (low-polarity compound) (53 mg, 0.130 mmol, 40%) as a white powder and the title Isomer 299-B (high-polarity compound) (20 mg, 0.0492 mmol, 15%) as colorless columnar crystals.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 13 hours under an argon atmosphere
  3. concentrationThe reaction mixture was then concentrated
  4. customThe residue thus obtained
  5. customwas separated
  6. custompurified by flash chromatography on a silica gel column (hexane:ethyl acetate=85:15)
  7. customThe solids thus obtained
  8. washeach washed with hexane, whereby
  9. customobtained

Sources & evidence

ORD record
ord-7791ecd081bf4d5c80c1a10a8cd2597b
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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