Hydrochloric Acid → 2-Fluoro-4-methoxy-1-(2-nitro-vinyl)-benzene

HRID 890376Notes

Reaction equation

HRID 890376 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[N+:12]([CH3:15])([O-:14])=[O:13].[OH-].[Na+].Cl>CO.O>[F:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=1[CH:4]=[CH:15][N+:12]([O-:14])=[O:13]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6375NitromethaneHCID 14798Sodium HydroxideHCID 27348732-Fluoro-4-methoxybenzaldehyde

Product 1

HCID 670319522-Fluoro-4-methoxy-1-(2-nitro-vinyl)-benzene

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

2-Fluoro-4-methoxy-benzaldehyde (1 equivalent) was dissolved in MeOH and chilled in an ice bath. Nitromethane (1 equivalent) was added. NaOH (1.05 equivalents) in water was added dropwise to the nitromethane/aldehyde solution, such that the temperature did not rise above 15° C. The reaction was then allowed to stir at 0° C. for 15 minutes. The reaction mixture was poured into concentrated HCl diluted with water. Product was extracted with EtOAc and washed with water, brine, and dried (Na2SO4). Solvent was removed to yield a yellow oil which was freeze-dried in 90% MeCN/H2O to give the product 2-fluoro-4-methoxy-1-(2-nitro-vinyl)-benzene, which was used without further purification.

Workup

  1. temperaturechilled in an ice bath
  2. customdid not rise above 15° C
  3. extractionProduct was extracted with EtOAc
  4. washwashed with water, brine
  5. dry with materialdried (Na2SO4)
  6. customSolvent was removed
  7. customto yield a yellow oil which
  8. dry with materialwas freeze-dried in 90% MeCN/H2O

Sources & evidence

ORD record
ord-ae5ee2d2a42b4ba7b52f4cbf288aebd1
Source dataset
uspto-grants-2006_02
Patent number
US06995269B2

Reaction notes

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