Benzoyl Peroxide → 3-chloro-2-nitrobenzyl bromide

HRID 1695294Notes

Reaction equation

HRID 1695294 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH3:9][C:10]1[C:15]([N+:16]([O-:18])=[O:17])=[C:14]([Cl:19])[CH:13]=[CH:12][CH:11]=1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:1][CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]([Cl:19])[C:15]=1[N+:16]([O-:18])=[O:17]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 793283-Chloro-2-nitrotoluene

Product 1

HCID 122325513-chloro-2-nitrobenzyl bromide

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

N-Bromosuccinimide (4.67 g, 26.23 mmol) was added to a stirred solution of 6-methyl-2-chloro-1-nitrobenzene (4.5 g, 26.23 mmol) in distilled carbon-tetrachloride. Benzoyl peroxide (0.01 g) was added to the reaction mixture and the mixture was refluxed for 8 h. The solid separated was filtered. The filtrate was concentrated to get the crude product, which was purified by using column chromatography (silica gel, pet.ether 60-80° C.) to obtain the title compound. Yield: 2.69 g, (41%); MS: m/e (Cl) 253 (M+1).

Workup

  1. temperaturethe mixture was refluxed for 8 h
  2. customThe solid separated
  3. filtrationwas filtered
  4. concentrationThe filtrate was concentrated
  5. customto get the crude product, which
  6. customwas purified
  7. customcolumn chromatography (silica gel, pet.ether 60-80° C.)

Sources & evidence

ORD record
ord-ee44502f0d84461dbf395657d8e12048
Source dataset
uspto-grants-2012_04
Patent number
US08163730B2

Reaction notes

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