m-Nitroacetophenone → 2-Chloro-1-(3-nitrophenyl)ethanone

HRID 2122056Notes

Reaction equation

HRID 2122056 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10](=[O:12])[CH3:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].S(Cl)([Cl:16])(=O)=O>C(OC(C)C)(C)C>[Cl:16][CH2:11][C:10]([C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)=[O:12]

Participants

4

Reactant 2

HCID 8494m-NitroacetophenoneHCID 24648Sulfuryl chloride

Product 1

HCID 74372-Chloro-1-(3-nitrophenyl)ethanoneYield 83.2%

Reagents, catalysts & solvents 1

HCID 7914Diisopropyl EtherSolvent

Procedure

3′-Nitroacetophenone (2.00 g) was dissolved in diisopropyl ether (12.1 ml) and sulfuryl chloride (6.70 g) was added all at once thereto at 22° C. and refluxed for 6.5 hours. The reaction mixture was allowed to cool to room temperature while stirring, and the precipitated solids were filtered and washed with diisopropyl ether. Drying under reduced pressure yielded the desired 2-chloro-3′-nitroacetophenone (2.01 g; 83.1%).

Workup

  1. temperaturerefluxed for 6.5 hours
  2. filtrationthe precipitated solids were filtered
  3. washwashed with diisopropyl ether
  4. customDrying under reduced pressure

Sources & evidence

ORD record
ord-51086aa603e145a4ab2999cf686bed9a
Source dataset
uspto-grants-2004_02
Patent number
US06696573B1

Reaction notes

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