Nitromethane → o-Bromo-nitrostyrene

HRID 380177Notes

Reaction equation

HRID 380177 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[N+:10]([CH3:13])([O-:12])=[O:11].[OH-].[Na+]>CO.O>[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[CH:13][N+:10]([O-:12])=[O:11]

Participants

6

Reactant 3

HCID 6375NitromethaneHCID 14798Sodium HydroxideHCID 811292-Bromobenzaldehyde

Product 1

HCID 187792o-Bromo-nitrostyrene

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of o-bromo-benzaldehyde (4 g, 21.6 mmol) and nitromethane (1.32 g, 21.6 mmol) in methanol (5 mL) was added NaOH (0.908 g, 22.7 nmol) in 1 mL of H2O. After 45 minutes, the precipitate was dissolved in 10 mL of H2O. The product precipitated out after the addition of 6N HCl. The product was recrystallized from ethanol; 0.312 g (6%).

Workup

  1. customThe product precipitated out
  2. additionafter the addition of 6N HCl
  3. customThe product was recrystallized from ethanol

Sources & evidence

ORD record
ord-3a7147da77924b19a957e1149337a4ea
Source dataset
uspto-grants-2001_10
Patent number
US06300501B1

Reaction notes

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