Iodine → 4-Ethyl-2-iodo-1-methoxybenzene

HRID 17094Notes

Reaction equation

HRID 17094 reaction equation
[I:1]I.[CH2:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)[CH3:4]>CO.S([O-])([O-])(=O)=O.[Ag+2]>[I:1][C:7]1[CH:6]=[C:5]([CH2:3][CH3:4])[CH:10]=[CH:9][C:8]=1[O:11][CH3:12]

Participants

5

Reactant 2

HCID 807IodineHCID 736901-Ethyl-4-methoxybenzene

Product 1

HCID 686869514-Ethyl-2-iodo-1-methoxybenzene

Reagents, catalysts & solvents 2

HCID 178418844HCID 178418844, compoundCatalystHCID 887MethanolSolvent2×

Procedure

A mixture of silver sulfate (1.15 g, 3.68 mmol) and iodine (0.93 g, 3.68 mmol) were stirred in methanol at room temperature. A solution of p-ethylanisole (0.50 g, 3.68 mmol) in methanol was added dropwise to the stirring mixture. The mixture was stirred at room temperature until completion of the reaction. It was filtered and the filtrate was concentrated. The residue was dissolved in methylene chloride, washed with 1 N sodium hydroxide, dried over anhydrous sodium sulfate, filtered and concentrated. The title compound was obtained without further purification. 1H NMR (CDCl3, 500 MHz) δ 7.64 (d, J=2.0 Hz, 1H), 7.15 (dd, J=8.5, 2.0 Hz, 1H), 6.77 (d, J=8.0 Hz, 1H), 3.88 (s, 3H), 2.58 (q, J=15.5, 8.0 Hz, 2H), 1.23 (t, J=7.5 Hz, 3H).

Workup

  1. filtrationIt was filtered
  2. concentrationthe filtrate was concentrated
  3. dissolutionThe residue was dissolved in methylene chloride
  4. washwashed with 1 N sodium hydroxide
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c82eff29b5eb41a6a8ee7e33a5e62a24
Source dataset
uspto-grants-2010_06
Patent number
US07737295B2

Reaction notes

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