Benzoyl Peroxide → 5-Bromo-2-(bromomethyl)-1,3-dichlorobenzene

HRID 1670810

Reaction equation

HRID 1670810 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([Cl:10])[C:5]([CH3:9])=[C:6]([Cl:8])[CH:7]=1.[Br:11]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]=[C:6]([Cl:8])[C:5]([CH2:9][Br:11])=[C:4]([Cl:10])[CH:3]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 6411555-Bromo-1,3-dichloro-2-methylbenzene

Product 1

HCID 594744985-Bromo-2-(bromomethyl)-1,3-dichlorobenzeneYield 87.8%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Heat to reflux a solution of 5-bromo-1,3-dichloro-2-methylbenzene (97 mg, 0.40 mmol), N-bromosuccinimide (76 mg, 0.425 mmol) and benzoyl peroxide (16 mg, 0.06 mmol) in CCl4 (5 mL) for 3 hours under N2. Cool the reaction to room temperature and concentrate to an orange residue. Purify the residue by silica gel chromatography eluting with hexanes to afford 112 mg (87%) of the product as white crystals.

Workup

  1. temperatureHeat
  2. temperatureCool
  3. customthe reaction to room temperature
  4. concentrationconcentrate to an orange residue
  5. customPurify the residue by silica gel chromatography
  6. washeluting with hexanes

Sources & evidence

ORD record
ord-528fb59ffc1f47bb9b46305a8d127424
Source dataset
uspto-grants-2011_08
Patent number
US07994176B2

Linked notes

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