N-bromobutanimide → HCID 23114238, compound

HRID 1850384Notes

Reaction equation

HRID 1850384 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH3:9][C:10]1[C:15]2[C:16](=[O:19])[CH2:17][O:18][C:14]=2[C:13]([CH3:20])=[C:12]([CH3:21])[CH:11]=1>C(Cl)Cl>[Br:1][C:11]1[C:12]([CH3:21])=[C:13]([CH3:20])[C:14]2[O:18][CH2:17][C:16](=[O:19])[C:15]=2[C:10]=1[CH3:9]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 11840233HCID 11840233, compound

Product 1

HCID 23114238HCID 23114238, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-bromosuccinimide (27.1 g, 152 mmol) was added to a solution of methylene chloride (200 mL) containing 4,6,7-trimethyl-1-benzofuran-3(2H)-one (20.7 g, 117 mmol) synthesized in Reference Example 44, and the mixture was stirred at room temperature for 24 hours. After that, the solvent was removed under reduced pressure, and water was added to the residue. The generated crystals were collected by filtration, and recrystallized from ethyl acetate to give 24.0 g of the title compound (yield: 80%).

Workup

  1. customsynthesized in Reference Example 44
  2. customAfter that, the solvent was removed under reduced pressure, and water
  3. additionwas added to the residue
  4. filtrationThe generated crystals were collected by filtration
  5. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-f9db25274728458396024b884853f9fb
Source dataset
uspto-grants-2015_02
Patent number
US08957069B2

Reaction notes

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