Benzoyl Peroxide → Tert-butyl 6-(bromomethyl)-2-[(tert-butoxycarbonyl)oxy]-3-(trifluoromethyl)benzoate

HRID 2076636Notes

Reaction equation

HRID 2076636 reaction equation
[Br:1]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[C:27]([O:31][C:32]([O:34][C:35]1[C:47]([C:48]([F:51])([F:50])[F:49])=[CH:46][CH:45]=[C:44]([CH3:52])[C:36]=1[C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])=[O:33])([CH3:30])([CH3:29])[CH3:28]>C(Cl)(Cl)(Cl)Cl>[Br:1][CH2:52][C:44]1[C:36]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])=[C:35]([O:34][C:32]([O:31][C:27]([CH3:28])([CH3:29])[CH3:30])=[O:33])[C:47]([C:48]([F:49])([F:50])[F:51])=[CH:46][CH:45]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 67119250Tert-butyl 2-[(tert-butoxycarbonyl)oxy]-6-methyl-3-(trifluoromethyl)benzoate

Product 1

HCID 67119234Tert-butyl 6-(bromomethyl)-2-[(tert-butoxycarbonyl)oxy]-3-(trifluoromethyl)benzoateYield 52%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

N-Bromosuccinimide (9.70 g, 54.5 mmol) and benzoyl peroxide (0.7 g) were added to a solution of tert-butyl 2-[(tert-butoxycarbonyl)oxy]-6-methyl-3-(trifluoromethyl)benzoate (18.6 g, 49.6 mmol) obtained in Example (28-4) in carbon tetrachloride (400 ml), and the mixture was heated under reflux for 5 hours. The temperature of the reaction mixture was returned to room temperature and the solvent was removed under reduced pressure. After n-hexane was added to the obtained residue and the mixture was filtered, the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluting solvent: toluene) to give tert-butyl 6-(bromomethyl)-2-[(tert-butoxycarbonyl)oxy]-3-(trifluoromethyl)benzoate (11.66 g, yield: 52%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 5 hours
  3. customwas returned to room temperature
  4. customthe solvent was removed under reduced pressure
  5. additionAfter n-hexane was added to the obtained residue
  6. filtrationthe mixture was filtered
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography (eluting solvent: toluene)

Sources & evidence

ORD record
ord-ec77beffeffa4b98ae52f157752c9123
Source dataset
uspto-grants-2011_04
Patent number
US07923573B2

Reaction notes

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