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

HRID 2098942Notes

Reaction equation

HRID 2098942 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) and 1-bromo-3-methylbut-2-ene (1616 μL, 13876 μmol) in DMF (30 mL), was added T21.3 (1593 mg, 13876 μmol). The mixture was stirred at room temperature for 1 hour, and then was 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 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 chromatography

Sources & evidence

ORD record
ord-807f6a9a2e4f4df588fedcdcc2b2737c
Source dataset
uspto-grants-2013_05
Patent number
US08450522B2

Reaction notes

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