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

HRID 1487207Notes

Reaction equation

HRID 1487207 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:5]=1[CH3:13].[Br:15]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:15][CH2:13][C:5]1[CH:6]=[C:7]([N+:10]([O-:12])=[O:11])[CH:8]=[CH:9][C:4]=1[C:3]([O:2][CH3:1])=[O:14]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 15088700Methyl 2-methyl-4-nitrobenzoate

Product 1

HCID 15088701Methyl 2-(bromomethyl)-4-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
80 °C

Procedure

2-methyl-4-nitrobenzoic acid methyl ester (696 mg, 3.57 mmol), azobisisbutyronitrile (58.6 mg, 0.357 mmol) and N-bromosuccinimide (785 mg, 4.46 mmol) were suspended in carbon tetrachloride (35 mL) in a sealed tube. The above mixture was flushed with nitrogen for 5 minutes and heated at 80° C. for 22 hours. After cooling, the solid was filtered off and the filtrate was concentrated to dryness to obtain the crude product methyl 2-(bromomethyl)-4-nitrobenzoate as a light-brown solid, which was used for the next step without purification.

Workup

  1. customThe above mixture was flushed with nitrogen for 5 minutes
  2. temperatureAfter cooling
  3. filtrationthe solid was filtered off
  4. concentrationthe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-c34485451b3f434b867472e16d7846d4
Source dataset
uspto-grants-2016_08
Patent number
US09428508B2

Reaction notes

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