Diiodomethane → HCID 23287853, compound

HRID 1740729Notes

Reaction equation

HRID 1740729 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>CN(C)C=O>[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

4

Reactant 2

HCID 6346DiiodomethaneHCID 18919733HCID 18919733, compound

Product 1

HCID 23287853HCID 23287853, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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

Sources & evidence

ORD record
ord-2e2defe77a07403bbb393b2861986556
Source dataset
uspto-grants-1999_10
Patent number
US05972925

Reaction notes

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