Iodobenzene → HCID 14669726, compound

HRID 1709264Notes

Reaction equation

HRID 1709264 reaction equation
[Mg].[C:2]1(I)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]1([S:15]([NH:18][CH2:19][C:20]([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:24][CH:23]=2)=[O:21])(=[O:17])=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[Cl-].[NH4+]>O1CCCC1.BrCCBr>[C:9]1([S:15]([NH:18][CH2:19][C:20]([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)=[CH:24][CH:23]=2)([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[OH:21])(=[O:17])=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 11575IodobenzeneHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 14579464N-[2-Oxo-2-[4-(phenylmethoxy)phenyl]ethyl]benzenesulfonamide

Product 1

HCID 14669726HCID 14669726, compoundYield 58.3%

Reagents, catalysts & solvents 2

HCID 78391,2-DibromoethaneCatalystHCID 8028TetrahydrofuranSolvent3×

Procedure

5.83 g of magnesium are suspended in 100 ml of dry tetrahydrofuran, and 5 drops of 1,2-dibromoethane are added thereto. After the mixture is stirred at room temperature, a solution of 28.3 g of phenyl iodide in 70 ml of tetrahydrofuran is added dropwise thereto. A solution of 7.65 g of 2-benzenesulfonylamino-1-(4-benzyloxyphenyl)ethanone in 100 ml of tetrahydrofuran is added dropwise to the reaction mixture under ice-cooling and stirring. The mixture is stirred at room temperature, and an aqueous ammonium chloride solution is added thereto. The mixture is extracted with ethyl acetate, and the extract is washed, dried and evaporated to remove the solvent. The residue is purified by silica gel flash column chromatography (solvent; chloroform), and recrystallized from a mixture of ethyl acetate and n-hexane. 5.37 g of 2-benzenesulfonylamino-1-(4-benzyloxyphenyl)-1-phenylethanol are obtained as colorless crystals. m.p. 147.5°-149° C.

Workup

  1. temperaturecooling
  2. stirringstirring
  3. stirringThe mixture is stirred at room temperature
  4. extractionThe mixture is extracted with ethyl acetate
  5. washthe extract is washed
  6. customdried
  7. customevaporated
  8. customto remove the solvent
  9. customThe residue is purified by silica gel flash column chromatography (solvent; chloroform)
  10. customrecrystallized from a mixture of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-9bd3d74916d54acc8f47129dff065b44
Source dataset
uspto-grants-1990_08
Patent number
US04948810

Reaction notes

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