N-bromobutanimide → HCID 23498955, compound

HRID 1836903Notes

Reaction equation

HRID 1836903 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9](/[CH:11]=[CH:12]/[C:13]2[C:22]([CH3:23])=[CH:21][C:20]3[C:19]([CH3:25])([CH3:24])[C:18](=[O:26])[CH2:17][C:16]([CH3:28])([CH3:27])[C:15]=3[CH:14]=2)[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[Br:29]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[CH3:1][C:2]1[CH:10]=[C:9](/[CH:11]=[CH:12]/[C:13]2[C:22]([CH2:23][Br:29])=[CH:21][C:20]3[C:19]([CH3:24])([CH3:25])[C:18](=[O:26])[CH2:17][C:16]([CH3:28])([CH3:27])[C:15]=3[CH:14]=2)[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 2

HCID 67184N-bromobutanimide2×HCID 23498958HCID 23498958, compound

Product 1

HCID 23498955HCID 23498955, compoundYield 59.3%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalyst2×HCID 5943Carbon TetrachlorideSolvent2×

Procedure

To a solution of 1.4 g (3.7 mmol) of methyl-4-[(E)-2-(5,5,8,8-tetramethyl-3-methyl-6-oxo-5,6,7,8-tetrahydro-naphthalen-2-yl)vinyl]-benzoic acid and 0.86 g (4.8 mmol) of N-bromosuccinimide in 50 ml carbon tetrachloride was added 45 mg (0.19 mmol) of benzoyl peroxide and the reaction was heated to reflux temperature. After 1 h, added additional 45 mg of benzoyl peroxide and 25 ml carbon tetrachloride. After 3 h total added 0.2 g N-bromosuccinimide. After 6 h total, cooled to room temperature, washed with 10% aqueous sodium bisulfite and brine, dried over sodium sulfate and adsorbed onto silica gel. Purified by flash chromatography (hexane-8% ethyl acetate/hexane) to give 1.0 g (59%) of methyl-4-[(E)-2-(5,5,8,8-tetramethyl-3-bromomethyl-6-oxo -5,6,7,8-tetrahydro-naphthalen-2-yl)vinyl]-benzoic acid.

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux temperature
  3. waitAfter 6 h total
  4. washwashed with 10% aqueous sodium bisulfite and brine
  5. dry with materialdried over sodium sulfate
  6. customPurified by flash chromatography (hexane-8% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-71c34b222f79428fa5f10a11557be032
Source dataset
uspto-grants-2004_08
Patent number
US06777418B2

Reaction notes

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