Dichloromethane → 4-Bromo-2-(bromomethyl)-1-chlorobenzene

HRID 576998

Reaction equation

HRID 576998 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[C:4]([CH3:9])[CH:3]=1.[Br:10]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.ClCCl>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[C:4]([CH2:9][Br:10])[CH:3]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 6098995-Bromo-2-chlorotoluene

Product 1

HCID 115582804-Bromo-2-(bromomethyl)-1-chlorobenzeneYield 70%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 4-bromo-1-chloro-2-methylbenzene (5.0 g, 24.0 mmol), N-bromosuccinimide (4.4 g, 25.0 mmol), and benzoyl peroxide (700 mg, 2.9 mmol) in anhydrous carbon tetrachloride (85 mL) was stirred at reflux for 4 hours. Dichloromethane (50 mL) was added. The mixture was extracted with 1 N NaOH (1×150 mL) and brine (1×150 mL). The organic extract was recovered, dried over MgSO4, filtered, evaporated, and dried in vacuo. The crude product was purified by flash chromatography (0-5% EtOAc/hexanes), affording 4-bromo-2-(bromomethyl)-1-chlorobenzene (4.76 g, 70% yield). The product was used without further purification.

Workup

  1. temperatureat reflux for 4 hours
  2. extractionThe mixture was extracted with 1 N NaOH (1×150 mL) and brine (1×150 mL)
  3. extractionThe organic extract
  4. customwas recovered
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customdried in vacuo
  9. customThe crude product was purified by flash chromatography (0-5% EtOAc/hexanes)

Sources & evidence

ORD record
ord-4f13da1817c04854b6bdc7ea6c2fc23c
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Linked notes

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