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

HRID 2427460

Reaction equation

HRID 2427460 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 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) to reflux 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. temperatureto reflux for 3 hours under N2
  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-56bc74df5037491aa0512ac34fab2992
Source dataset
uspto-grants-2011_06
Patent number
US07968585B2

Linked notes

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