2-Chloro-4-nitrotoluene → 1-(Bromomethyl)-2-chloro-4-nitrobenzene
Reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH3:11].[Br:12]N1C(=O)CCC1=O>ClC(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:12][CH2:11][C:3]1[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=1[Cl:1]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture of 2-chloro-4-nitrotoluene (0.20 g, 1.17 mmol), N-bromosuccinimide (0.228 g, 1.28 mmol) and benzoyl peroxide (0.014 g, 0.058 mmol) in tetrachloromethane (7 mL) was irradiated (500 W lamp) at reflux overnight. The reaction mixture was concentrated to give a yellow oil/solid (0.391 g) which was used directly in the next step without further purification.
Workup
- customwas irradiated (500 W lamp)
- temperatureat reflux overnight
- concentrationThe reaction mixture was concentrated
Sources & evidence
- ORD record
- ord-e90ef17a050242bdac678cbd4138b979
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07700599B2
Reaction notes
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