N-bromobutanimide → Methyl 4-(bromomethyl)-3-nitrobenzoate

HRID 1072864Notes

Reaction equation

HRID 1072864 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:13]=1[CH3:14])[C:7]([O:9][CH3:10])=[O:8])([O-:3])=[O:2].[Br:15]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.CC(N=NC(C#N)(C)C)(C#N)C>[Br:15][CH2:14][C:13]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[N+:1]([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 81816Methyl 4-methyl-3-nitrobenzoate

Product 1

HCID 13399987Methyl 4-(bromomethyl)-3-nitrobenzoateYield 127.1%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of methyl 3-nitro-4-methylbenzoate (4.147 g), N-bromo-succinimide (7.12 g) and AIBN (0.40 g) in carbon tetrachloride (30 ml) was stirred at 70° C. for 42 hr. After cooling, the insoluble matter was filtered off and the filtrate was concentrated to give an oil (7.40 g) containing the object compound.

Workup

  1. temperatureAfter cooling
  2. filtrationthe insoluble matter was filtered off
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-2009f8b6329047329d881d3b06a34e1c
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Reaction notes

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