Allyl bromide → HCID 23117635, compound

HRID 1178323Notes

Reaction equation

HRID 1178323 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[CH:5]([N:14]=[CH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]([Cl:13])[CH:7]=1)[CH3:2].[CH2:23](Br)[CH:24]=[CH2:25].C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH:15](=[N:14][C:5]([C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]([Cl:13])[CH:7]=1)([CH2:25][CH:24]=[CH2:23])[C:4]([O:3][CH2:1][CH3:2])=[O:22])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 58696280HCID 58696280, compound

Product 1

HCID 23117635HCID 23117635, compoundYield 94.2%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl(benzylidene-amino)-(3,4-dichlorophenyl)-acetate (1.41 mol) was dissolved in ethyl acetate (2.3 L). Allyl bromide (341 g), potassium carbonate (390 g), and tetrabutylammonium bromide (45 g) were added to the resultant mixture, followed by refluxing for 2.5 hours. The reaction mixture was left to cool to room temperature. The mixture was sequentially washed with water and saturated brine, dried over sodium sulfate anhydrate, and concentrated under reduced pressure, to thereby give the title compound (500 g, 94%).

Workup

  1. temperatureby refluxing for 2.5 hours
  2. waitThe reaction mixture was left
  3. washThe mixture was sequentially washed with water and saturated brine
  4. dry with materialdried over sodium sulfate anhydrate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0e63fdad07464e2ba3a1878b7b301eee
Source dataset
uspto-grants-2007_10
Patent number
US07276511B2

Reaction notes

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