Water → 1-Fluoro-3-((E)-2-nitro-vinyl)-5-propoxy-benzene

HRID 20437Notes

Reaction equation

HRID 20437 reaction equation
C([O-])(=O)C.[NH4+].[F:6][C:7]1[CH:8]=[C:9]([CH:12]=[C:13]([O:15][CH2:16][CH2:17][CH3:18])[CH:14]=1)[CH:10]=O.[N+:19]([CH3:22])([O-:21])=[O:20].O>C(O)(=O)C>[F:6][C:7]1[CH:14]=[C:13]([O:15][CH2:16][CH2:17][CH3:18])[CH:12]=[C:9](/[CH:10]=[CH:22]/[N+:19]([O-:21])=[O:20])[CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 862368003-Fluoro-5-propoxybenzaldehyde

Product 1

HCID 685582311-Fluoro-3-((E)-2-nitro-vinyl)-5-propoxy-benzeneYield 69.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
140 °C

Procedure

Add ammonium acetate (2.63 g, 34.08 mmol) to 3-fluoro-5-propoxy-benzaldehyde (2.25 g, 12.35 mmol) and nitromethane (3.09 g, 50.63 mmol) in acetic acid (41 mL) at room temperature and heat in 140° C. oil bath for 3 hours. Cool to room temperature and pour into water. Extract with ethyl acetate, dry over magnesium sulfate, filter and concentrate to afford 1.94 g (69.8%) of the desired compound as an oil.

Workup

  1. temperatureCool to room temperature
  2. extractionExtract with ethyl acetate
  3. dry with materialdry over magnesium sulfate
  4. filtrationfilter
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-a207859cfb484bf3b0098ee913e5b2b4
Source dataset
uspto-grants-2010_06
Patent number
US07745438B2

Reaction notes

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