Water → HCID 23359193, compound

HRID 232874Notes

Reaction equation

HRID 232874 reaction equation
[I-:1].[K+].Br[C:4]1[CH:20]=[CH:19][C:7]2[C:8](=[O:18])[C:9]3[CH:16]=[C:15]([OH:17])[CH:14]=[CH:13][C:10]=3[O:11][CH2:12][C:6]=2[CH:5]=1.O.C(OCC)(=O)C>CN(C)P(=O)(N(C)C)N(C)C.[Cu]I>[OH:17][C:15]1[CH:14]=[CH:13][C:10]2[O:11][CH2:12][C:6]3[CH:5]=[C:4]([I:1])[CH:20]=[CH:19][C:7]=3[C:8](=[O:18])[C:9]=2[CH:16]=1

Participants

7

Reactant 4

HCID 962WaterHCID 4875Potassium IodideHCID 8857Ethyl AcetateHCID 23359184HCID 23359184, compound

Product 1

HCID 23359193HCID 23359193, compoundYield 37.3%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
160 °C

Procedure

10.35 g of copper (I) iodide and 26.9 g of potassium iodide were added to 3.3 g of 8-bromo-2-hydroxy-11-oxo-6,11-dihydrodibenz[b,e]oxepine obtained in Reference example 27 dissolved in 33 ml of hexamethylphosphoric acid triamide and the mixture was stirred under nitrogen stream at 160° C. for 4 hours. After 300 ml of water and 400 ml of ethyl acetate were added to the reaction mixture, the organic layer was separated, washed with water and dried over anhydrous sodium sulfate. The residue obtained by removing the solvent was washed with chloroform to obtain 1.42 g of the title compound.

Workup

  1. customobtained in Reference example 27
  2. customthe organic layer was separated
  3. washwashed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe residue obtained
  6. customby removing the solvent
  7. washwas washed with chloroform

Sources & evidence

ORD record
ord-42f56274e78746898fd4b053ab168c78
Source dataset
uspto-grants-1997_01
Patent number
US05591752

Reaction notes

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