Water → 1,2-Difluoro-4-(2-nitroethenyl)benzene

HRID 216206Notes

Reaction equation

HRID 216206 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[CH:5]=O.[N+:11]([CH3:14])([O-:13])=[O:12].C([O-])(=O)C.[NH4+].O>C(O)(=O)C>[F:10][C:9]1[CH:8]=[CH:7][C:4]([CH:5]=[CH:14][N+:11]([O-:13])=[O:12])=[CH:3][C:2]=1[F:1]

Participants

6

Reactant 4

HCID 962WaterHCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 5880883,4-Difluorobenzaldehyde

Product 1

HCID 668019841,2-Difluoro-4-(2-nitroethenyl)benzene

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 3,4-difluorobenzaldehyde (5.05 g), nitromethane (5.3 mL) and ammonium acetate (6.3 g) in glacial acetic acid (60 mL) is heated at 110° C. for 16 hours, allowed to cool and poured into water (300 mL). The solution is extracted with EtOAc (2×200 mL). The combined extract is washed with 10% NaHCO3, water and dried over sodium sulfate, filtered and evaporated in vacuo to afford 1,2-difluoro-4-(2-nitro-vinyl)benzene (4.2 g). MS: 198 (M+H); 1H NMR (300 MHz, CDCl3) □7.9 (1H, d, J=10 Hz); 7.5 (1H, d, 10 Hz); 7.3 (2H, m); 6.95-7.15 (1H, m).

Workup

  1. temperatureto cool
  2. extractionThe solution is extracted with EtOAc (2×200 mL)
  3. extractionThe combined extract
  4. washis washed with 10% NaHCO3, water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-6eb64e71583d47b0b77ae1dc3b5292a3
Source dataset
uspto-grants-2012_06
Patent number
US08193183B2

Reaction notes

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