Nitromethane → 4-Bromo-2-chloro-1-(2-nitroethenyl)benzene

HRID 1853911Notes

Reaction equation

HRID 1853911 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[C:4]([Cl:10])[CH:3]=1.Cl.CN.CC([O-])=O.[Na+].[N+:19]([CH3:22])([O-:21])=[O:20]>O>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH:22][N+:19]([O-:21])=[O:20])=[C:4]([Cl:10])[CH:3]=1

Participants

6

Reactant 4

HCID 6375NitromethaneHCID 517045Sodium AcetateHCID 6364545Methylamine hydrochlorideHCID 141091094-Bromo-2-chlorobenzaldehyde

Product 1

HCID 670804594-Bromo-2-chloro-1-(2-nitroethenyl)benzeneYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 4-bromo-2-chlorobenzaldehyde (7.5 g, 34 mmol) in nitromethane was added methylamine hydrochloride (1.3 g, 22 mmol), NaOAc (1.8 g, 22 mmol). The mixture was vigorously stirred for 18 h at room temperature. The reaction mixture was diluted with water (60 mL) and extracted with CH2Cl2 (3×100 mL), organic phases dried (Na2SO4), evaporated to afford the desired product (8.5 g, 95%) as a light yellow oil: ESI MS m/z 262 [C8H5BrClNO2+H]+.

Workup

  1. extractionextracted with CH2Cl2 (3×100 mL), organic phases
  2. dry with materialdried (Na2SO4)
  3. customevaporated

Sources & evidence

ORD record
ord-d13e1b44f6c64784b0095c79295a0c96
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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