Nitroethane → 1-Methanesulfonyl-4-(2-nitro-propenyl)-2-trifluoromethyl-benzene

HRID 908191Notes

Reaction equation

HRID 908191 reaction equation
[CH3:1][S:2]([C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][C:6]=1[C:13]([F:16])([F:15])[F:14])(=[O:4])=[O:3].[N+:17]([CH2:20][CH3:21])([O-:19])=[O:18].C([O-])(=O)C.[NH4+]>ClCCl>[CH3:1][S:2]([C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[C:20]([N+:17]([O-:19])=[O:18])[CH3:21])=[CH:7][C:6]=1[C:13]([F:16])([F:15])[F:14])(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 6587NitroethaneHCID 517165Ammonium AcetateHCID 714799064-Methanesulfonyl-3-trifluoromethyl-benzaldehyde

Product 1

HCID 673913281-Methanesulfonyl-4-(2-nitro-propenyl)-2-trifluoromethyl-benzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred mixture of 4-methanesulfonyl-3-trifluoromethyl-benzaldehyde (Example 5001a) (12 g, 47 mmol), nitroethane (27.5 ml, 380 mol) and ammonium acetate (1.22 g, 16 mmol) is heated at reflux under argon for 18 hours. The mixture is concentrated to give an oil which is dissolved in dichloromethane (200 ml) and washed with water (3×200 ml), followed by brine (200 ml). The organic extract is dried (MgSO4), filtered and the solvent removed to give the product as red oil. This is used immediately in the next step.

Workup

  1. temperatureis heated
  2. temperatureat reflux under argon for 18 hours
  3. concentrationThe mixture is concentrated
  4. customto give an oil which
  5. washwashed with water (3×200 ml)
  6. extractionThe organic extract
  7. dry with materialis dried (MgSO4)
  8. filtrationfiltered
  9. customthe solvent removed

Sources & evidence

ORD record
ord-bbebb2d3796b4798bf0cc7e489898e26
Source dataset
uspto-grants-2011_09
Patent number
US08017608B2

Reaction notes

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