Nitromethane → 4-Bromo-2-methoxy-1-(2-nitrovinyl)benzene

HRID 510579Notes

Reaction equation

HRID 510579 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[C:4]([O:10][CH3:11])[CH:3]=1.Cl.CN.C([O-])(=O)C.[Na+].[N+:20]([CH3:23])([O-:22])=[O:21]>O.ClCCl>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH:23][N+:20]([O-:22])=[O:21])=[C:4]([O:10][CH3:11])[CH:3]=1

Participants

7

Reactant 4

HCID 6375NitromethaneHCID 517045Sodium AcetateHCID 6364545Methylamine hydrochlorideHCID 110530414-Bromo-2-methoxybenzaldehyde

Product 1

HCID 670803454-Bromo-2-methoxy-1-(2-nitrovinyl)benzene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A suspension of 4-bromo-2-methoxybenzaldehyde (1.55 g; 7.2 mmol), methylamine hydrochloride (0.31 g; 50.4 mmol) and sodium acetate (0.38 g; 4.6 mmol) in 3 mL of nitromethane was stirred at ambient temperature. After stirring for 14.5 hours the mixture was diluted with 20 mL water and 40 mL dichloromethane, and the mixture was transferred to a separatory funnel. After shaking, the organic layer was dried over sodium sulfate and evaporated to give 1.74 g of 4-bromo-2-methoxy-1-(2-nitrovinyl)benzene as a light yellow solid. MS (apci, neg) m/z=257.

Workup

  1. stirringAfter stirring for 14.5 hours the mixture
  2. customthe mixture was transferred to a separatory funnel
  3. stirringAfter shaking
  4. dry with materialthe organic layer was dried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-5c50234dca6e4a73b2e402e5496bb654
Source dataset
uspto-grants-2015_08
Patent number
US09096567B2

Reaction notes

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