Azobisisobutyronitrile → Methyl 3-(bromomethyl)-2-nitrobenzoate

HRID 1586758Notes

Reaction equation

HRID 1586758 reaction equation
[N+:1]([C:4]1[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7])([O-:3])=[O:2].[Br:15]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[N+:1]([C:4]1[C:13]([CH2:14][Br:15])=[CH:12][CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 79621Benzoic acid, 3-methyl-2-nitro-, methyl ester

Product 1

HCID 22509333Methyl 3-(bromomethyl)-2-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Methyl 2-nitro-3-methylbenzoate (15.3 gm) was suspended in carbon tetrachloride (45 mL) along with N-bromosuccinimide (15 3 gm) and heated to reflux. 2,2'-Azobis(2-methylpropionitrile) (AIBN) (0.4 gm) was added to the refluxing solution in four equal portions over 48 hours. The reaction was cooled to room temperature, filtered, and concentrated. The residue consisted of a mixture of starting material, desired product, and dibrominated material which were difficult to separate and so were used in the next step without purification.

Workup

  1. temperatureheated to reflux
  2. filtrationfiltered
  3. concentrationconcentrated
  4. additionThe residue consisted of a mixture of starting material, desired product, and dibrominated material which
  5. customto separate
  6. customso were used in the next step without purification

Sources & evidence

ORD record
ord-b826b036ebb145d39ce59f71411d453c
Source dataset
uspto-grants-1993_06
Patent number
US05216003

Reaction notes

Loading…