4-Iodobenzoyl chloride → 1-(4-Iodophenyl)-2-methylpropan-1-one

HRID 1805307Notes

Reaction equation

HRID 1805307 reaction equation
[CH:1]([Mg]Cl)([CH3:3])[CH3:2].[I:6][C:7]1[CH:15]=[CH:14][C:10]([C:11](Cl)=[O:12])=[CH:9][CH:8]=1>C1COCC1>[I:6][C:7]1[CH:15]=[CH:14][C:10]([C:11](=[O:12])[CH:1]([CH3:3])[CH3:2])=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 743734-Iodobenzoyl chlorideHCID 178418918HCID 178418918, compound

Product 1

HCID 197647831-(4-Iodophenyl)-2-methylpropan-1-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 2.0 M solution of Isopropylmagnesium chloride (10 ml, 20 mmol) was added dropwise (30 min), under nitrogen, to a stirred solution of freshly distilled 4-iodobenzoyl chloride (5.32 g, 20 mmol) and Fe(acac)3 (0.35 g, 1 mmol) in 150 ml of dry THF at room temperature. After addition, the stirring was continued for 10 min at the same temperature. The reaction was quenched by pouring the mixture into dilute hydrochloric acid and extracted with several portions of ether. The combined ether extracts were washed with aq. NaHCO3, water, and dried over Na2SO4. Removal of the organic solvents under vacuum gave the product as colorless oil. And the crude product was used for the next step without further purification.

Workup

  1. customat room temperature
  2. additionAfter addition
  3. customThe reaction was quenched
  4. additionby pouring the mixture into dilute hydrochloric acid
  5. extractionextracted with several portions of ether
  6. washThe combined ether extracts were washed with aq. NaHCO3, water
  7. dry with materialdried over Na2SO4
  8. customRemoval of the organic solvents under vacuum

Sources & evidence

ORD record
ord-5fe0118e4e4f46fcbde708b466514924
Source dataset
uspto-grants-2013_01
Patent number
US08354443B2

Reaction notes

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