Carbon Tetrachloride → 1-(Bromomethyl)-2-chloro-3-methyl-5-nitrobenzene

HRID 374542

Reaction equation

HRID 374542 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[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.ClC(Cl)(Cl)Cl>O>[Br:13][CH2:8][C:7]1[CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[CH:4]=[C:3]([CH3:12])[C:2]=1[Cl:1]

Participants

6

Reactant 4

HCID 5943Carbon TetrachlorideHCID 7187Benzoyl Peroxide2×HCID 67184N-bromobutanimideHCID 99205692-Chloro-1,3-dimethyl-5-nitrobenzene

Product 1

HCID 189972501-(Bromomethyl)-2-chloro-3-methyl-5-nitrobenzeneYield 70.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 129 g of 2-chloro-1,3-dimethyl-5-nitrobenzene, 125 g of 1-bromo-2,5-pyrrolidinedione, 12 g of dibenzoyl peroxide and 1200 ml of tetrachloromethane was stirred for 2 hours at reflux temperature using a water separator. Twice there was added an extra portion of 20 g of dibenzoyl peroxide during a refluxing period of 29 hours. After cooling, the reaction mixture was washed with water, dried, filtered and evaporated. The residue was purified by column chromatography (silica gel; CH2Cl2 /hexane 50:50). The eluent of the desired fraction was evaporated, yielding 130 g (70.2%) of 1-(bromomethyl)-2-chloro-3-methyl-5-nitrobenzene (interm. 5).

Workup

  1. temperatureat reflux temperature
  2. temperatureAfter cooling
  3. washthe reaction mixture was washed with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography (silica gel; CH2Cl2 /hexane 50:50)
  8. customThe eluent of the desired fraction was evaporated

Sources & evidence

ORD record
ord-a2d6793df1834518a51fc3a7edf07cbf
Source dataset
uspto-grants-1996_01
Patent number
US05480912

Linked notes

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