Sodium Iodide → 2'-Fluoro-2-(1-hydroxy-2,2-dimethyl-but-3-enyl)-5'-methoxy-biphenyl-4-carboxylic acid methyl ester

HRID 404382Notes

Reaction equation

HRID 404382 reaction equation
[I-].[Na+].[In].Br[CH2:5][CH:6]=[C:7]([CH3:9])[CH3:8].[CH3:10][O:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[CH:22][C:21]=2[F:28])=[C:16]([CH:29]=[O:30])[CH:15]=1)=[O:13]>CN(C=O)C.CCOC(C)=O.O>[CH3:10][O:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[CH:22][C:21]=2[F:28])=[C:16]([CH:29]([OH:30])[C:7]([CH3:9])([CH3:8])[CH:6]=[CH2:5])[CH:15]=1)=[O:13]

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 700922-Butene, 1-bromo-3-methyl-HCID 5359967IndiumHCID 574676302'-Fluoro-2-formyl-5'-methoxy-biphenyl-4-carboxylic acid methyl ester

Product 1

HCID 574676322'-Fluoro-2-(1-hydroxy-2,2-dimethyl-but-3-enyl)-5'-methoxy-biphenyl-4-carboxylic acid methyl esterYield 92%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixed solution of sodium iodide (2080 mg, 13876 μmol), indium (2000 mg, 6938 μmol, commercially available from Sigma-Aldrich, St. Louis, Mo., USA) and 1-bromo-3-methylbut-2-ene (1616 μL, 13876 μmol, commercially available from Sigma-Aldrich, St. Louis, Mo., USA) in DMF (30 mL), was added 21.3 (1593 mg, 13876 μmol). The mixture was stirred at room temperature for 1 hour and then diluted with EtOAc and water. The organic phase was washed with water and brine and then dried over anhydrous sodium sulfate. After filtration, the organic solvent was removed in vacuo to give a residue which was purified by CombiFlash® chromatography to give the product as an oil (2.30 g, 92%). MS ESI m/e: 376.1 (M+18)+.

Workup

  1. washThe organic phase was washed with water and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationAfter filtration
  4. customthe organic solvent was removed in vacuo
  5. customto give a residue which
  6. customwas purified by CombiFlash® chromatography

Sources & evidence

ORD record
ord-4cf4e3a1dc454cb89b56dbcc7201a34a
Source dataset
uspto-grants-2014_06
Patent number
US08748462B2

Reaction notes

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