Nitromethane → 1-Chloro-2-fluoro-4-(2-nitroethenyl)benzene

HRID 2279459Notes

Reaction equation

HRID 2279459 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[F:10].C([O-])(=O)C.[NH4+].[N+:16]([CH3:19])([O-:18])=[O:17]>CC(O)=O.O>[Cl:1][C:2]1[CH:9]=[CH:8][C:5](/[CH:6]=[CH:19]/[N+:16]([O-:18])=[O:17])=[CH:4][C:3]=1[F:10]

Participants

6

Reactant 3

HCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 27249854-Chloro-3-Fluorobenzaldehyde

Product 1

HCID 616522621-Chloro-2-fluoro-4-(2-nitroethenyl)benzeneYield 13.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 4-chloro-3-fluorobenzaldehyde (10 g, 63.07 mmol) and ammonium acetate (4.861 g, 63.07 mmol) in HOAc (50 mL) was added nitromethane (14.12 mL, 252.3 mmol) and the reaction mixture was heated to reflux (120° C. oil bath) for 18 h. The reaction was cooled and diluted with water. The reaction mixture was filtered and solids were purified by SiO2 chromatography eluting with a EtOAc/hexane gradient (0 to 5% EtOAc) to afford 1.736 g (13.65%) of (E)-1-chloro-2-fluoro-4-(2-nitrovinyl)benzene (86).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureThe reaction was cooled
  3. filtrationThe reaction mixture was filtered
  4. customsolids were purified by SiO2 chromatography
  5. washeluting with a EtOAc/hexane gradient (0 to 5% EtOAc)

Sources & evidence

ORD record
ord-cf956c768afb4cb5902f3d57c9649c41
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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