Ethyl 4-iodobenzoate → 2-(4-Iodophenyl)propan-2-ol

HRID 1796954Notes

Reaction equation

HRID 1796954 reaction equation
[I:1][C:2]1[CH:12]=[CH:11][C:5](C(OCC)=O)=[CH:4][CH:3]=1.[CH3:13][Mg+].[Br-].CC[O:18][CH2:19][CH3:20]>CCOCC>[CH3:13][C:19]([OH:18])([CH3:20])[C:5]1[CH:11]=[CH:12][C:2]([I:1])=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 142891Ethyl 4-iodobenzoateHCID 178467672HCID 178467672, compound

Product 1

HCID 539961442-(4-Iodophenyl)propan-2-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a cooled (ice/H2O) solution of 2.76 g of ethyl 4-iodobenzoate (prepared as described in Step 1) in 10 ml of anhyd. Et2O was added, over a 5 minutes period, 26.5 ml of 1.52M CH3MgBr/Et2O solution. The mixture was stirred at ice bath temperature for 2.5 hours and then quenched by slow addition of 6 ml of H2O. The reaction mixture was filtered and the solid residue rinsed with ether. The combined filtrates were dried over MgSO4 and concentrated under vacuum to provide the title compound as a clear yellowish liquid.

Workup

  1. customquenched by slow addition of 6 ml of H2O
  2. filtrationThe reaction mixture was filtered
  3. washthe solid residue rinsed with ether
  4. dry with materialThe combined filtrates were dried over MgSO4
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-d267b5b2eea64e9a9f57c342296ae43d
Source dataset
uspto-grants-2006_04
Patent number
US07034026B2

Reaction notes

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