Water → HCID 21287218, compound

HRID 868534Notes

Reaction equation

HRID 868534 reaction equation
[Cl:1][C:2]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:3]=1[CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]([CH3:14])=[CH2:13].[Br:20]N1C(=O)CCC1=O.O>C(Cl)(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[Cl:1][C:2]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:3]=1[CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]([CH2:14][Br:20])=[CH2:13]

Participants

6

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 14349367HCID 14349367, compound

Product 1

HCID 21287218HCID 21287218, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

2-[2-(2,4-Dichlorobenzyloxy)phenyl]-1-propene (1.0 g, 3.41 mmole), N-bromosuccinimide (0.61 g, 3.41 mmole) and azobisisobutyronitrile (2.8 mg, 0.017 mmole) were suspended in carbon tetrachloride (4 ml) and the suspension was refluxed with stirring for 12 hours. Then, the mixture was poured into water (30 ml) and extracted with ethyl acetate (50 ml). The extract was washed with water (50 ml) and dried over anhydrous soidum sulfate. After distilling off the solvent under reduced pressure, the residue was subjected to chromatography on a silica gel column and eluted with n-hexane to obtain the title compound (0.52 g, 41.0%). 1H-NMR (CDCl3, δ): 4.50 (s, 2H, CH2Br), 5.20 (s, 2H, ##STR49## 5.33 (d, 1H, =CH), 5.57 (d, 1H, =CH), 6.80-7.57 (m, 7H, aromatic).

Workup

  1. temperaturethe suspension was refluxed
  2. extractionextracted with ethyl acetate (50 ml)
  3. washThe extract was washed with water (50 ml)
  4. dry with materialdried over anhydrous soidum sulfate
  5. distillationAfter distilling off the solvent under reduced pressure
  6. washeluted with n-hexane

Sources & evidence

ORD record
ord-fa4b0d739da4490196cb6edb4d0b005b
Source dataset
uspto-grants-1988_10
Patent number
US04780471

Reaction notes

Loading…