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

HRID 1780808Notes

Reaction equation

HRID 1780808 reaction equation
[CH3:1][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Br:15]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)Cl>[Br:15][CH2:1][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 601165Methyl 2-methyl-3-nitrobenzoate

Product 1

HCID 1487795Methyl 2-(bromomethyl)-3-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5 (1 g) in chloroform (70 mL) was added N-bromosuccinimide (0.82 g) and azobis(isobutyronitrile) (0.010 g). A light source was directed onto the flask and the mixture was refluxed for 18 h. The solution was cooled to 0° C., a precipitate was filtered, and flitrate was concentrated in vacuo to obtain the crude product. Purification on silica gel with hexane/ethyl acetate 9/1 afforded the product as a solid. NMR (300 MHz, CDC3) δ 8.10 (1H, d, J=9 Hz), 7.95 (1H,d, J=9 Hz), 7.54 (1H,t, J=9 Hz), 5.14 (2H, s), 3.99 (3H, s).

Workup

  1. temperaturethe mixture was refluxed for 18 h
  2. filtrationa precipitate was filtered
  3. concentrationflitrate was concentrated in vacuo
  4. customto obtain the crude product
  5. customPurification on silica gel with hexane/ethyl acetate 9/1

Sources & evidence

ORD record
ord-3a79039356274f5f827f04de0c65d7eb
Source dataset
uspto-grants-1997_05
Patent number
US05631280

Reaction notes

Loading…