Isopropyl iodide → 4-Ethyl-1-iodo-2-isopropoxy-benzene

HRID 1167308Notes

Reaction equation

HRID 1167308 reaction equation
[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([I:10])=[C:7]([OH:9])[CH:8]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].I[CH:18]([CH3:20])[CH3:19]>O>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([I:10])=[C:7]([O:9][CH:18]([CH3:20])[CH3:19])[CH:8]=1)[CH3:2]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 229961995-Ethyl-2-iodophenol

Product 1

HCID 229962054-Ethyl-1-iodo-2-isopropoxy-benzeneYield 80.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5-ethyl-2-iodophenol (1.0 g, 4 mmol), potassium carbonate (1.10 g, 8 mmol) and 2-iodopropane (0.80 mL, 8 mmol) was heated at reflux for 6 h. The reaction mixture was cooled to room temperature and water was added. The mixture was extracted with diethyl ether. The combined organic extracts were washed with brine and dried over anhydrous magnesium sulfate. The solid was then filtered off, and the filtrate was concentrated in vacuo. Purification of the residue by flash chromatography (Biotage system, KP-Sil™ 32-63 μm, 60 Å silica gel) eluting with hexanes, 5% ethyl acetate in hexanes yielded 4-ethyl-1-iodo-2-isopropoxy-benzene (0.93 g, 80%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 6 h
  3. extractionThe mixture was extracted with diethyl ether
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationThe solid was then filtered off
  7. concentrationthe filtrate was concentrated in vacuo
  8. customPurification of the residue by flash chromatography (Biotage system, KP-Sil™ 32-63 μm, 60 Å silica gel)
  9. washeluting with hexanes, 5% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-6749a1b09e734fc5a711df162cc1bb87
Source dataset
uspto-grants-2003_09
Patent number
US06617346B1

Reaction notes

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