Iodoethane → 4-(1,1-Dimethylethyl)-2-ethoxy-1-iodobenzene

HRID 2425578Notes

Reaction equation

HRID 2425578 reaction equation
[C:1]([C:5]1[CH:6]=[CH:7][C:8]([I:12])=[C:9]([OH:11])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:19](I)[CH3:20]>C(O)C.C(OCC)C>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([I:12])=[C:9]([O:11][CH2:19][CH3:20])[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 117478025-tert-Butyl-2-iodophenol

Product 1

HCID 672460864-(1,1-Dimethylethyl)-2-ethoxy-1-iodobenzeneYield 99%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

The mixture of 5-tert-butyl-2-iodo-phenol (132.7 g, 480.6 mmol), potassium carbonate (265.7 g, 1923 mmol) and ethyl iodide (76.9 mL, 961.3 mmol) in ethanol (1.125 mL) was heated at reflux overnight. Upon cooling to room temperature, the reaction mixture was diluted with diethyl ether. The white solids were filtered off, and the filtrate was concentrated in vacuo to give 4-tert-butyl-2-ethoxy-1-iodo-benzene (144.7 g) as pale yellow oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. filtrationThe white solids were filtered off
  4. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-73f996cd49394a1ba2d7b43b916c9472
Source dataset
uspto-grants-2011_06
Patent number
US07964724B2

Reaction notes

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