Nitromethane → (E)-1-Chloro-4-(4-(2-nitrovinyl)phenoxy)-2-(trifluoromethyl)benzene

HRID 474567Notes

Reaction equation

HRID 474567 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[CH:14]=[CH:13][C:10]([CH:11]=O)=[CH:9][CH:8]=2)=[CH:4][C:3]=1[C:17]([F:20])([F:19])[F:18].C([O-])(=O)C.[NH4+].[N+:26]([CH3:29])([O-:28])=[O:27]>CC(O)=O>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[CH:14]=[CH:13][C:10](/[CH:11]=[CH:29]/[N+:26]([O-:28])=[O:27])=[CH:9][CH:8]=2)=[CH:4][C:3]=1[C:17]([F:20])([F:19])[F:18]

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 866661874-(4-Chloro-3-(trifluoromethyl)phenoxy)benzaldehyde

Product 1

HCID 67775160(E)-1-Chloro-4-(4-(2-nitrovinyl)phenoxy)-2-(trifluoromethyl)benzeneYield 99.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

To the mixture of 4-(4-chloro-3-(trifluoromethyl)phenoxy)benzaldehyde (600 mg, 1.996 mmol), ammonium acetate (77 mg, 0.998 mmol) in AcOH (5 mL) was added nitromethane (0.323 mL, 5.99 mmol). It was heated at 120° C. for 3 h, then concentrated in vacuo. The residue was dissolved in DCM (30 ml), washed with saturated NaHCO3 aqueous solution (20 ml×2), and brine. The organic phase was collected, dried over Na2SO4, filtered, concentrated to provide the title compound as a brown solid (680 mg, 66.4% yield), which was used without further purification. LCMS: rt=4.17 min, [M+H+]=344.1

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in DCM (30 ml)
  3. washwashed with saturated NaHCO3 aqueous solution (20 ml×2), and brine
  4. customThe organic phase was collected
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-6fcbf7a1f8794f02bb7ce84bda8dcce2
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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