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

HRID 1810462Notes

Reaction equation

HRID 1810462 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-3e0fba73c06047e49a038a231eaaa97b
Source dataset
uspto-grants-2013_01
Patent number
US08362044B2

Reaction notes

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