4-Nitrobenzoyl chloride → 1-(4-Nitrophenyl)-1-propanone

HRID 1171036Notes

Reaction equation

HRID 1171036 reaction equation
[CH2:1]([Mg]Cl)[CH3:2].[N+:5]([C:8]1[CH:16]=[CH:15][C:11]([C:12](Cl)=[O:13])=[CH:10][CH:9]=1)([O-:7])=[O:6]>C1COCC1.O.[Cl-].[Cl-].[Zn+2].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N+:5]([C:8]1[CH:9]=[CH:10][C:11]([C:12](=[O:13])[CH2:1][CH3:2])=[CH:15][CH:16]=1)([O-:7])=[O:6]

Participants

7

Reactant 2

HCID 85024-Nitrobenzoyl chlorideHCID 178461633HCID 178461633, compound

Product 1

HCID 947261-(4-Nitrophenyl)-1-propanoneYield 40%

Reagents, catalysts & solvents 4

HCID 3007855ZincchlorideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent4×

Procedure

A solution of 0.5M ZnCl2 in THF (60 mL, 30 mmol) in THF (20 mL) at room temperature was treated with 2M ethyl magnesium chloride in THF (15 mL, 30 mmol) dropwise via syringe, cooled with an ice bath for about 10 minutes, stirred at room temperature for 20 minutes, cooled to 0° C., and treated sequentially with Pd(PPh3)4 (1.73 g, 1.5 mmol) and a solution of 4-nitrobenzoyl chloride (6.12 g, 33 mmol) in THF (20 mL). The mixture was stirred at 0° C. for 40 minutes, diluted with water and extracted three times with ethyl acetate. The combined extracts were washed with saturated Na2CO3, water, and brine, dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 6:1 hexanes/ethyl acetate to provide 2.17 g (40%) of the desired product. Rf=0.6 (3:1 hexanes/ethyl acetate).

Workup

  1. temperaturecooled with an ice bath for about 10 minutes
  2. temperaturecooled to 0° C.
  3. stirringThe mixture was stirred at 0° C. for 40 minutes
  4. extractionextracted three times with ethyl acetate
  5. washThe combined extracts were washed with saturated Na2CO3, water, and brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe concentrate was purified by flash column chromatography on silica gel with 6:1 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-314e5893ca454ed191fc01d7482381b3
Source dataset
uspto-grants-2010_11
Patent number
US07829570B2

Reaction notes

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