Succinimide → HCID 131728576, compound

HRID 2262404Notes

Reaction equation

HRID 2262404 reaction equation
[CH3:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5]([C:12]([F:15])([F:14])[F:13])=[CH:4][C:3]=1[B:16]1[O:24][C:21]([CH3:23])([CH3:22])[C:18]([CH3:20])([CH3:19])[O:17]1.C1C(=O)N([Br:32])C(=O)C1.C1(=O)NC(=O)CC1>CC(N=NC(C#N)(C)C)(C#N)C.C(Cl)(Cl)(Cl)Cl>[Br:32][CH2:1][C:2]1[C:7]([C:8]([F:9])([F:11])[F:10])=[CH:6][C:5]([C:12]([F:14])([F:15])[F:13])=[CH:4][C:3]=1[B:16]1[O:17][C:18]([CH3:20])([CH3:19])[C:21]([CH3:23])([CH3:22])[O:24]1

Participants

6

Reactant 3

HCID 11439SuccinimideHCID 67184N-bromobutanimideHCID 131324503HCID 131324503, compound

Product 1

HCID 131728576HCID 131728576, compoundYield 90.7%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

2-Methyl-3,5-bis(trifluoromethyl)phenylboronic acid pinacol ester (24a, 2.0 g, 5.6 mmol) and 50 ml CCl4 were placed in a 250 ml round-bottom flask. NBS (1.05, 5.88 mmol, 1.05 eq) and AIBN (0.013 g, 0.078 mmol, 0.014 eq) were added and the reaction mixture was refluxed for 3 h in the presence of 75 W incandescent bulb. After 3 h the solution was cooled down to room temperature allowing the succinimide to precipitate out. The solid was filtered off. The solvent was removed and oily product was collected. The crude product was purified by triturating with hexane which resulted in 90% pure product (25a, 2.2 g, 90% yield).

Workup

  1. temperaturethe reaction mixture was refluxed for 3 h in the presence of 75 W incandescent bulb
  2. customto precipitate out
  3. filtrationThe solid was filtered off
  4. customThe solvent was removed
  5. customoily product was collected
  6. customThe crude product was purified
  7. customby triturating with hexane which

Sources & evidence

ORD record
ord-122e4d543b3b48348c977af5750b430b
Source dataset
uspto-grants-2010_12
Patent number
US07851225B2

Reaction notes

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