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

HRID 596070Notes

Reaction equation

HRID 596070 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].O>C(O)(=O)C>[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 4

HCID 962WaterHCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 27249854-Chloro-3-Fluorobenzaldehyde

Product 1

HCID 616522621-Chloro-2-fluoro-4-(2-nitroethenyl)benzeneYield 41.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 4-chloro-3-fluorobenzaldehyde (8 g, 50.5 mmol) and ammonium acetate (9.72 g, 126 mmol) in acetic acid (168 mL) was added nitromethane (8.16 mL, 151 mmol). The reaction mixture was heated at reflux for 5 h and cooled down. Water (100 mL) was added, and the mixture was stirred at room temperature for 1 h. The solid was filtered, washed by water, and dried under vacuum. The solid was purified by flash chromatography (0-20% EtOAc/heptane) to yield clean product 4.2 g in 41% yield. 1H NMR (400 MHz, CDCl3) δ ppm 7.92 (d, J=13.7 Hz, 1H), 7.54 (d, J=13.8 Hz, 1H), 7.49 (d, J=7.5 Hz, 1H), 7.33 (dd, J=2.0, 9.3 Hz, 1H), 7.31-7.28 (m, 1H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 5 h
  3. temperaturecooled down
  4. filtrationThe solid was filtered
  5. washwashed by water
  6. customdried under vacuum
  7. customThe solid was purified by flash chromatography (0-20% EtOAc/heptane)

Sources & evidence

ORD record
ord-69799ac9e80c4471982030568394e4b5
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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