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

HRID 908199Notes

Reaction equation

HRID 908199 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

Conditions

Temperature
115 °C

Procedure

A stirred mixture of 3-fluoro-4-methanesulfonyl-benzaldehyde (Example 68a) (20 g, 99 mmol), nitroethane (58 ml, 811 mmol) and ammonium acetate (2.29 g, 29 mmol) is heated at reflux (115° C.) under argon for 18 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 is used immediately in the next step.

Workup

  1. temperatureis heated
  2. concentrationThe mixture is concentrated
  3. customto give an oil which
  4. washwashed with water (2×200 ml)
  5. extractionThe organic extract
  6. dry with materialis dried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent removed

Sources & evidence

ORD record
ord-79c54b7011f74a60aaa8f5c454541f0c
Source dataset
uspto-grants-2011_09
Patent number
US08017608B2

Reaction notes

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