Iodoethane → HCID 22929833, compound

HRID 1296022Notes

Reaction equation

HRID 1296022 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:7](I)[CH3:8].[Br:10][C:11]1[CH:12]=[C:13]([C:22]([CH3:25])([CH3:24])[CH3:23])[C:14]([O:18][CH2:19][O:20][CH3:21])=[C:15]([OH:17])[CH:16]=1.C(OCC)(=O)C>C(#N)C>[Br:10][C:11]1[CH:16]=[C:15]([O:17][CH2:7][CH3:8])[C:14]([O:18][CH2:19][O:20][CH3:21])=[C:13]([C:22]([CH3:23])([CH3:24])[CH3:25])[CH:12]=1

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 22929986HCID 22929986, compound

Product 1

HCID 22929833HCID 22929833, compoundYield 76.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Cesium carbonate (10.05 g, 30.9 mmol) and EtI (2.58 ml, 32.2 mmol) were added to a solution of the 5-bromo-3-(tert-butyl)-2-(methoxymethoxy)phenol (7.76 g, 26.8 mmol) in acetonitrile and the mixture was stirred at room temperature for 3 hours. Ethyl acetate was added and the reaction mixture was washed with water and brine in that order. The organic layer was dried over anhydrous magnesium sulfate and then the residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (6.5 g) as a yellow oil.

Workup

  1. washthe reaction mixture was washed with water and brine in that order
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-736602992edb40d8949c4ac6719844d3
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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