Sodium Iodide → Methyl-2-(4-iodophenyl)-2-methyl-propionate

HRID 330819Notes

Reaction equation

HRID 330819 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]([C:7]1[CH:12]=[CH:11][C:10](Br)=[CH:9][CH:8]=1)([CH3:6])[CH3:5].[I-:15].[Na+].CNCCNC>O1CCOCC1.CCOC(C)=O.[Cu]I>[CH3:1][O:2][C:3](=[O:14])[C:4]([C:7]1[CH:12]=[CH:11][C:10]([I:15])=[CH:9][CH:8]=1)([CH3:6])[CH3:5]

Participants

7

Reactant 3

HCID 5238Sodium IodideHCID 8070N,N'-DimethylethylenediamineHCID 3651431Methyl 2-(4-bromophenyl)-2-methylpropanoate

Product 1

HCID 21107277Methyl-2-(4-iodophenyl)-2-methyl-propionate

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

To 0.45 g (1.7 mmol) 2-(4-bromo-phenyl)-2-methyl-propionic acid methyl ester (WO2008/002671) in 1.5 mL 1,4-dioxane are added 34 mg (0.18 mmol) copper(I) iodide, 0.53 g (3.5 mmol) sodium iodide and 0.04 mL (0.35 mmol) N,N′-dimethylethylendiamine under inert gas atmosphere. The mixture is stirred at 110° C. for 12 h. After cooling, the mixture is diluted with EtOAc and washed with 5% ammonia and water. The organic layer is dried over sodium sulphate. The solvent is evaporated to yield the desired product.

Workup

  1. temperatureAfter cooling
  2. washwashed with 5% ammonia and water
  3. dry with materialThe organic layer is dried over sodium sulphate
  4. customThe solvent is evaporated

Sources & evidence

ORD record
ord-7abb273025a24a32a20970e1b100f87e
Source dataset
uspto-grants-2014_11
Patent number
US08877754B2

Reaction notes

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