o-Chloranil → HCID 12752103, compound

HRID 1476694Notes

Reaction equation

HRID 1476694 reaction equation
[N+](=[CH:3][C:4]([C:6]1[O: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>[O:7]1[CH:8]=[CH:9][CH:10]=[C:6]1[C:4]([CH:3]1[O:22][C:13]2[C:12]([Cl:11])=[C:17]([Cl:18])[C:16]([Cl:19])=[C:15]([Cl:20])[C:14]=2[O:21]1)=[O:5]

Participants

4

Reactant 2

HCID 73252o-ChloranilHCID 57364289HCID 57364289, compound

Product 1

HCID 12752103HCID 12752103, compoundYield 16.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2-diazo-1-(furan-2-yl)ethanone (900 mg, 6.61 mmol) and 3,4,5,6-tetrachlorocyclohexa-3,5-diene-1,2-dione (846 mg, 10.05 mmol) were combined in dry benzene (10 ml) and refluxed vigorously for 6 hours. The solvent was evaporated to dryness, and the resulting crude material was subjected to column chromatography using 100-200 mesh range silica gel and an ethyl acetate/hexane solvent system. The crude material was a mixture of two compounds, which were separated by column chromatography. Crystallization from acetone yielded furan-2-yl(4,5,6,7-tetrachlorobenzo[d][1,3]dioxol-2-yl)methanone as a yellow solid (200 mg, 16.4%).

Workup

  1. temperaturerefluxed vigorously for 6 hours
  2. customThe solvent was evaporated to dryness
  3. additiona mixture of two compounds, which
  4. customwere separated by column chromatography
  5. customCrystallization from acetone

Sources & evidence

ORD record
ord-a744c483aec84f1ca6937c5e0a48b993
Source dataset
uspto-grants-2016_08
Patent number
US09402397B2

Reaction notes

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