N-bromobutanimide → Ethyl 3-[5-bromomethyl-1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl]propionate

HRID 1814626Notes

Reaction equation

HRID 1814626 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[N:6]([CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:5]2=[O:19].[Br:20]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.CC(N=NC(C#N)(C)C)(C#N)C>[Br:20][CH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[N:6]([CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:5]2=[O:19]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 22501918Ethyl 3-[5-methyl-1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl]propionate

Product 1

HCID 22502293Ethyl 3-[5-bromomethyl-1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl]propionateYield 104.1%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

The material from step 1 (27.3 g, 0.10 mol) was dissolved in carbon tetrachloride (50 mL), and N-bromosuccinimide (19.5 g, 0.11 mol) and AIBN (200 mg) was added. The mixture was refluxed for 5 hours, filtered by suction, and the filtrate was concentrated to give 35.4 g yellow oil.

Workup

  1. temperatureThe mixture was refluxed for 5 hours
  2. filtrationfiltered by suction
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-ccfb98f5c3144715becf2911a8b32e1a
Source dataset
uspto-grants-2005_04
Patent number
US06875760B2

Reaction notes

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