Nitroethane → 2-Fluoro-1-methanesulfonyl-4-(2-nitro-propenyl)-benzene

HRID 1672507Notes

Reaction equation

HRID 1672507 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[S:10]([CH3:13])(=[O:12])=[O:11])[CH:5]=O.[N+:14]([CH2:17][CH3:18])([O-:16])=[O:15].C([O-])(=O)C.[NH4+]>C(Cl)(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:17]([N+:14]([O-:16])=[O:15])[CH3:18])[CH:7]=[CH:8][C:9]=1[S:10]([CH3:13])(=[O:12])=[O:11]

Participants

5

Reactant 3

HCID 6587NitroethaneHCID 517165Ammonium AcetateHCID 212517323-Fluoro-4-methanesulfonylbenzaldehyde

Product 1

HCID 665884842-Fluoro-1-methanesulfonyl-4-(2-nitro-propenyl)-benzene

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A stirred mixture of 3-fluoro-4-methanesulfonyl-benzaldehyde (Example AA1) (24 g, 0.119 mol), nitroethane (70 ml, 0.97 mol) and ammonium acetate (2.75 g, 35 mmol) was heated at reflux under argon for 24 hours. The mixture was concentrated to give an oil which was dissolved in chloroform (200 ml) and washed with water (2×200 ml), followed by brine (100 ml). The organic extract was dried (MgSO4), filtered and the solvent removed to give the product as an orange oil. This was used immediately in the next step.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under argon for 24 hours
  3. concentrationThe mixture was concentrated
  4. customto give an oil which
  5. washwashed with water (2×200 ml)
  6. extractionThe organic extract
  7. dry with materialwas dried (MgSO4)
  8. filtrationfiltered
  9. customthe solvent removed

Sources & evidence

ORD record
ord-bc6a4a68e5ca4ed398e994ab8d049222
Source dataset
uspto-grants-2011_08
Patent number
US07998990B2

Reaction notes

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