Succinimide → Methyl 2-(bromomethyl)-5-fluoro-3-nitrobenzoate

HRID 1869321Notes

Reaction equation

HRID 1869321 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[C:6]([N+:11]([O-:13])=[O:12])[C:5]=1[CH3:14].[Br:16]N1C(=O)CCC1=O.C1(=O)NC(=O)CC1>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[C:6]([N+:11]([O-:13])=[O:12])[C:5]=1[CH2:14][Br:16]

Participants

6

Reactant 3

HCID 11439SuccinimideHCID 67184N-bromobutanimideHCID 44203026Methyl 5-fluoro-2-methyl-3-nitrobenzoate

Product 1

HCID 68679319Methyl 2-(bromomethyl)-5-fluoro-3-nitrobenzoateYield 76.1%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

2.37 g (11.12 mmol) of 5-fluoro-2-methyl-3-nitrobenzoic acid methyl ester is added in 35 ml of carbon tetrachloride and mixed with 2.24 g (12.24 mmol) of N-bromosuccinimide and 5.4 mg of benzoyl peroxide. After four days of refluxing, the succinimide is suctioned off (glass-fiber filter) after cooling, and then the filtrate is spun in until a dry state is reached. Chromatography on a Flashmaster yields 2.47 g (75.9%) of the desired compound.

Workup

  1. temperatureAfter four days of refluxing
  2. filtration(glass-fiber filter)
  3. temperatureafter cooling

Sources & evidence

ORD record
ord-1dd251351e73412286c65efd08fed19f
Source dataset
uspto-grants-2009_12
Patent number
US07638515B2

Reaction notes

Loading…