Dimethylformamide → 2-Bromo-5-nitrobenzoyl chloride

HRID 1531275Notes

Reaction equation

HRID 1531275 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4](O)=[O:5].C(Cl)(=O)C([Cl:17])=O.CN(C=O)C>C(Cl)Cl.CN(C=O)C>[Br:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([Cl:17])=[O:5]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 2430252-Bromo-5-nitrobenzoic acid

Product 1

HCID 114710722-Bromo-5-nitrobenzoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-bromo-5-nitrobenzoic acid (1.00 g, 4.06 mmol) in methylene chloride (15 mL) is added oxalyl chloride (1.42 mL, 16.24 mmol) followed by 1 drop DMF. Addition of DMF results in vigorous gas evolution. After 1.5 h, the reaction mixture is concentrated under reduced pressure to give an oil which is used as is without purification.

Workup

  1. customresults in vigorous gas evolution
  2. concentrationthe reaction mixture is concentrated under reduced pressure
  3. customto give an oil which
  4. customas is without purification

Sources & evidence

ORD record
ord-c83b5af817fc41bdb8042d21c857dcde
Source dataset
uspto-grants-2001_03
Patent number
US06197798B1

Reaction notes

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