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

HRID 1092967Notes

Reaction equation

HRID 1092967 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 64a) (24 g, 0.119 mol), nitroethane (70 ml, 0.97 mol) and ammonium acetate (2.75 g, 35 mmol) is heated at reflux under argon for 24 hours. The mixture is concentrated to give an oil which is dissolved in chloroform (200 ml) and washed with water (2×200 ml), followed by brine (100 ml). The organic extract is 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. temperatureis heated
  2. temperatureat reflux under argon for 24 hours
  3. concentrationThe mixture is concentrated
  4. customto give an oil which
  5. washwashed with water (2×200 ml)
  6. extractionThe organic extract
  7. dry with materialis dried (MgSO4)
  8. filtrationfiltered
  9. customthe solvent removed

Sources & evidence

ORD record
ord-ec3d2cb9ce6a41dda4b8182114ebff86
Source dataset
uspto-grants-2012_03
Patent number
US08129541B2

Reaction notes

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