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

HRID 2098953Notes

Reaction equation

HRID 2098953 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:12][C:11]=1[CH:20]=[O:21].Br[CH2:23][CH:24]=[C:25]([CH3:27])[CH3:26].[I-].[Na+].[In]>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:12][C:11]=1[CH:20]([OH:21])[C:25]([CH3:27])([CH3:26])[CH:24]=[CH2:23]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 700922-Butene, 1-bromo-3-methyl-2×HCID 5359967Indium2×HCID 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 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of T29.3 (0.38 g, 1.3 mmol), 1-bromo-3-methylbut-2-ene (commercially available from Aldrich) (0.31 mL, 2.6 mmol) and sodium iodide (0.40 g, 2.6 mmol) in DMF (8 mL), was added indium (0.30 g, 2.6 mmol). The resulting mixture was stirred at room temperature for 1 hour and then additional 1-bromo-3-methylbut-2-ene (100 mg) and indium (100 mg) were added and the mixture was stirred at room temperature for one more hour. The reaction was quenched with water (20 mL) and extracted with EtOAc (200 mL). The organic phase was washed with brine, dried over anhydrous sodium sulfate, and filtered. After removing solvent, the residue was purified by flash chromatography (silica gel, 1:4 EtOAc/hexane) and gave product (T29.4), in 94% yield.

Workup

  1. stirringthe mixture was stirred at room temperature for one more hour
  2. customThe reaction was quenched with water (20 mL)
  3. extractionextracted with EtOAc (200 mL)
  4. washThe organic phase was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customAfter removing solvent
  8. customthe residue was purified by flash chromatography (silica gel, 1:4 EtOAc/hexane)
  9. customgave product (T29.4)

Sources & evidence

ORD record
ord-6894f659d9a247fb8e10ed13c9bc294c
Source dataset
uspto-grants-2013_05
Patent number
US08450522B2

Reaction notes

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