N-bromobutanimide → HCID 87358217, compound

HRID 926925Notes

Reaction equation

HRID 926925 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]([C:12]1[CH:17]=[C:16]([CH3:18])[CH:15]=[CH:14][C:13]=1[I:19])([O:8][CH2:9][O:10][CH3:11])[C:4]([F:7])([F:6])[F:5].[Br:22]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:22][CH2:18][C:16]1[CH:15]=[CH:14][C:13]([I:19])=[C:12]([C:3]([O:8][CH2:9][O:10][CH3:11])([C:4]([F:7])([F:6])[F:5])[C:2]([F:1])([F:20])[F:21])[CH:17]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 88909600HCID 88909600, compound

Product 1

HCID 87358217HCID 87358217, compoundYield 76.5%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
78 °C

Procedure

Compound 3 (2.51 g, 5.86 mmol), benzoyl peroxide (57 mg, 256 μmol) and N-bromosuccinimide (1.038 g, 8.79 mmol) were dissolved in 25 mL carbon tetrachloride. The solution was degassed, placed under nitrogen atmosphere and heated 15 h at 78° C. After cooling to room temperature, the mixture was filtered, and the solid washed with carbon tetrachloride. The filtrate was evaporated under reduced pressure to give a residue which was purified over silica gel using heptane/acetone as eluant to give 2.27 g (4.48 mmol, 76% yield) of a white solid.

Workup

  1. customThe solution was degassed
  2. temperatureAfter cooling to room temperature
  3. filtrationthe mixture was filtered
  4. washthe solid washed with carbon tetrachloride
  5. customThe filtrate was evaporated under reduced pressure
  6. customto give a residue which
  7. customwas purified over silica gel

Sources & evidence

ORD record
ord-a50cda34288b4bbcb1a5152bee271861
Source dataset
uspto-grants-2016_03
Patent number
US09290421B2

Reaction notes

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