Azobisisobutyronitrile → Methyl 2-(bromomethyl)-4-nitrobenzoate

HRID 473481Notes

Reaction equation

HRID 473481 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:5]=1[CH3:13].[Br:15]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N.C1(=O)NC(=O)CC1>C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:5]=1[CH2:13][Br:15]

Participants

6

Reactant 4

HCID 6547AzobisisobutyronitrileHCID 11439SuccinimideHCID 67184N-bromobutanimideHCID 15088700Methyl 2-methyl-4-nitrobenzoate

Product 1

HCID 15088701Methyl 2-(bromomethyl)-4-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

In accordance with general method T, 4.70 g (24.00 mmol) of (1) are dissolved in 30 ml of carbon tetrachloride, with heating, and 5.00 g (28.00 mmol) of N-bromosuccinimide and 2 spatula tips of azobisisobutyronitrile are then added. The mixture is refluxed for 6 h with irradiation with a 500 W spotlight. On cooling to room temperature, succinimide separates out, and is filtered off. The filtrate is evaporated on a rotary evaporator in order to obtain the product as a yellow oil. Yield: 5.85 g (88.8%)

Workup

  1. temperaturewith heating
  2. temperatureThe mixture is refluxed for 6 h with irradiation with a 500 W spotlight
  3. filtrationis filtered off
  4. customThe filtrate is evaporated on a rotary evaporator in order

Sources & evidence

ORD record
ord-803e764bf1dd4180ac70060ea340f3a1
Source dataset
uspto-grants-2014_01
Patent number
US08633312B2

Reaction notes

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