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

HRID 2122054Notes

Reaction equation

HRID 2122054 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>[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 67%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

3′-Nitroacetophenone (2.00 g) was suspended in methyl t-butyl ether (12.1 ml), and sulfuryl chloride (4.90 g) was dropwise added thereto at 20° C. over 15 minutes. After stirring for 2 hours, precipitated solids were filtered and washed with methyl t-butyl ether. Drying under reduced pressure yielded the desired 2-chloro-3′-nitroacetophenone (1.62 g; 67.0%).

Workup

  1. customprecipitated solids
  2. filtrationwere filtered
  3. washwashed with methyl t-butyl ether
  4. customDrying under reduced pressure

Sources & evidence

ORD record
ord-bcabfbf82f8e4999a0c5bba15cd4169a
Source dataset
uspto-grants-2004_02
Patent number
US06696573B1

Reaction notes

Loading…