Benzoyl Peroxide → 2-(4-Bromo-3-bromomethyl-phenyl)-propan-2-ol

HRID 2197382Notes

Reaction equation

HRID 2197382 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:11])([CH3:10])[CH3:9])=[CH:4][C:3]=1[CH3:12].[Br:13]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:11])([CH3:9])[CH3:10])=[CH:4][C:3]=1[CH2:12][Br:13]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 574198672-(4-Bromo-3-methylphenyl)propan-2-ol

Product 1

HCID 574198682-(4-Bromo-3-bromomethyl-phenyl)-propan-2-ol

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

2-(4-Bromo-3-methyl-phenyl)-propan-2-ol (0.916 g, 4.0 mmol) in CCl4 (30 mL) was treated with N-bromosuccinimide (0.750 g, 4.2 mmol) and benzoyl peroxide (0.050 g, 0.2 mmol), and the reaction was refluxed under a halogen lamp for 2 hours. After cooling to room temperature, the mixture was partitioned between CH2Cl2 and H2O, and the organic layer was dried, filtered, and concentrated. The residue was purified by silica gel chromatography to give the title compound.

Workup

  1. temperaturethe reaction was refluxed under a halogen lamp for 2 hours
  2. customthe mixture was partitioned between CH2Cl2 and H2O
  3. customthe organic layer was dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-2f430538f11443a08e1d5bcde57798e5
Source dataset
uspto-grants-2012_12
Patent number
US08338484B2

Reaction notes

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