N-bromobutanimide → HCID 23498913, compound

HRID 1836898Notes

Reaction equation

HRID 1836898 reaction equation
[CH2:1]([O:3][C:4](=[O:32])[C:5]1[CH:10]=[CH:9][C:8](/[CH:11]=[CH:12]/[C:13]2[C:22]([CH3:23])=[CH:21][C:20]3[C:19]([CH3:25])([CH3:24])[CH:18]([O:26][C:27](=[O:29])[CH3:28])[CH2:17][C:16]([CH3:31])([CH3:30])[C:15]=3[CH:14]=2)=[CH:7][CH:6]=1)[CH3:2].[Br:33]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:32])[C:5]1[CH:6]=[CH:7][C:8](/[CH:11]=[CH:12]/[C:13]2[C:22]([CH2:23][Br:33])=[CH:21][C:20]3[C:19]([CH3:25])([CH3:24])[CH:18]([O:26][C:27](=[O:29])[CH3:28])[CH2:17][C:16]([CH3:31])([CH3:30])[C:15]=3[CH:14]=2)=[CH:9][CH:10]=1)[CH3:2]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 23498918HCID 23498918, compound

Product 1

HCID 23498913HCID 23498913, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 0.68 g (1.57 mmol) of Ethyl-4-[(E)-2-(5,5,8,8-Tetramethyl-3-methyl-6-acetoxy-5,6,7,8-tetrahydro-naphthalen-2-yl)vinyl]benzoate, 0.36 g (2.03 mmol) of N-bromosuccinimide and 0.019 g (0.078 mmol) of benzoyl peroxide in 15 mL of carbon tetrachloride was heated at reflux. After 3 hours the reaction was cooled to room temperature, washed with 10% aqueous sodium bisulfite and brine, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography (gradient elution, hexane-5% ethyl acetate/hexane) to give 0.45 g (56%) of Ethyl-4-[(E)-2-(5,5,8,8-Tetramethyl-3-bromomethyl-6-acetoxy-5,6,7,8-tetrahydro-naphthalen-2-yl)vinyl]benzoate (M+=512).

Workup

  1. temperatureat reflux
  2. washwashed with 10% aqueous sodium bisulfite and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography (gradient elution, hexane-5% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-71596dfa09b04e2586e6862a461bf69f
Source dataset
uspto-grants-2004_08
Patent number
US06777418B2

Reaction notes

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