N-bromobutanimide → Methyl 2-(bromomethyl)-4-nitrobenzoate

HRID 1947628Notes

Reaction equation

HRID 1947628 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH3:9][O:10][C:11](=[O:22])[C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][C:13]=1[CH3:21].C1CCC(N=NC2(C#N)CCCCC2)(C#N)CC1>C(Cl)(Cl)(Cl)Cl>[CH3:9][O:10][C:11](=[O:22])[C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][C:13]=1[CH2:21][Br:1]

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 749781,1'-Azobis(cyclohexanecarbonitrile)HCID 15088700Methyl 2-methyl-4-nitrobenzoate

Product 1

HCID 15088701Methyl 2-(bromomethyl)-4-nitrobenzoateYield 96.1%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

N-Bromosuccinimide (2.18 g, 12.30 mmol) was added to a stirred solution of 2-methyl-4-nitro-benzoic acid methyl ester (2 g, 10.25 mmol) and ABCN (626 mg, 2.56 mmol) in carbon tetra-chloride (80 ml) at room temperature. The reaction was heated at reflux for 2 hrs and then allowed to cool to room temperature and stirred for 15 hrs. The solvent was evaporated in vacuo and the resulting residue filtered through a pad of silica (eluting with dichloromethane). The solvent was evaporated in vacuo to afford the title compound as a yellow solid (2.70 g, 96%). HPLC retention time 4.49 min. Mass spectrum (ES+) m/z 256 (M+H).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 2 hrs
  3. customThe solvent was evaporated in vacuo
  4. filtrationthe resulting residue filtered through a pad of silica (eluting with dichloromethane)
  5. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-84ca2e2d0ac24421ace9a8081310ae9e
Source dataset
uspto-grants-2013_03
Patent number
US08399481B2

Reaction notes

Loading…