Diiodomethane → HCID 23287853, compound

HRID 850314Notes

Reaction equation

HRID 850314 reaction equation
[OH:1][C:2]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:3]=1[C:4]([C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:7]=1[OH:13])=[O:5].I[CH2:20]I>>[Cl:18][C:15]1[CH:16]=[CH:17][C:2]2[O:1][CH2:20][O:13][C:7]3[CH:8]=[CH:9][C:10]([Cl:12])=[CH:11][C:6]=3[C:4](=[O:5])[C:3]=2[CH:14]=1

Participants

3

Reactant 2

HCID 6346DiiodomethaneHCID 18919733HCID 18919733, compound

Product 1

HCID 23287853HCID 23287853, compoundYield 96%

Conditions

Temperature
105 °C

Procedure

2,2'-Dihydroxy-5,5'-dichlorobenzophenone (12.1 g, 0.042 mol, prepared similarly as described in Journal of the American Chemical Society 77, 543 (1955)) and diiodomethane (11.9 g, 0.044 mol) were dissolved in dry N,N-dimethylformamnide (226 ml). Dried and powdered potassium carbonate (8.3 g) was added and the mixture was heated at 105° C. for 5 h and left overnight at room temperature. The reaction mixture was poured on ice (220 g). The precipitate was collected by filtration after 0.5 h and dissolved in diethyl ether (500 ml). The organic layer was washed with 5% sodium hydroxide (50 ml), dried over MgSO4 and evaporated in vacuo, affording 12 g (96%) of 2,10-dichloro-12H-dibenzo[d,g][1,3]-dioxocin-12-one as a solid.

Workup

  1. dissolutionwere dissolved in dry N,N-dimethylformamnide (226 ml)
  2. customDried
  3. additionpowdered potassium carbonate (8.3 g) was added
  4. additionThe reaction mixture was poured on ice (220 g)
  5. filtrationThe precipitate was collected by filtration after 0.5 h
  6. dissolutiondissolved in diethyl ether (500 ml)
  7. washThe organic layer was washed with 5% sodium hydroxide (50 ml)
  8. dry with materialdried over MgSO4
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-3e628e44b4a14c9da24d2f6ca24c7cb1
Source dataset
uspto-grants-2000_01
Patent number
US06017915

Reaction notes

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