o-Chloranil → HCID 12752104, compound

HRID 1476691Notes

Reaction equation

HRID 1476691 reaction equation
[N+](=[CH:3][C:4]([C:6]1[S:7][CH:8]=[CH:9][CH:10]=1)=[O:5])=[N-].[Cl:11][C:12]1[C:13](=[O:22])[C:14](=[O:21])[C:15]([Cl:20])=[C:16]([Cl:19])[C:17]=1[Cl:18]>C1C=CC=CC=1>[Cl:11][C:12]1[C:13]2[O:22][CH:3]([C:4]([C:6]3[S:7][CH:8]=[CH:9][CH:10]=3)=[O:5])[O:21][C:14]=2[C:15]([Cl:20])=[C:16]([Cl:19])[C:17]=1[Cl:18]

Participants

4

Reactant 2

HCID 73252o-ChloranilHCID 85325068HCID 85325068, compound

Product 1

HCID 12752104HCID 12752104, compoundYield 43.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2-diazo-1-(thiophen-2-yl)ethanone (2.3 g, 0.0151 mol) and 3,4,5,6-tetrachlorocyclohexa-3,5-diene-1,2-dione (3.36 g, 0.0136 mol) were then combined in dry benzene (25 mL) and refluxed vigorously for 6 hours. The solvent was then evaporated to dryness, and the crude material was subjected to column chromatography using 100-200 mesh silica gel and 15% ethyl acetate-hexane solvent system. Evaporation of the solvent yielded (4,5,6,7-tetrachlorobenzo[d][1,3]dioxol-2-yl)(thiophen-2-yl)methanone as an orange solid (2.2 g, 43.4%).

Workup

  1. temperaturerefluxed vigorously for 6 hours
  2. customThe solvent was then evaporated to dryness
  3. customEvaporation of the solvent

Sources & evidence

ORD record
ord-0fd8ff75caee430f8334662434a329f3
Source dataset
uspto-grants-2016_08
Patent number
US09402397B2

Reaction notes

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