Water → 2-(4-Bromophenyl)-3,3,3-trifluoronitropropene

HRID 277969Notes

Reaction equation

HRID 277969 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[C:9]([F:12])([F:11])[F:10])=[CH:4][CH:3]=1.[CH3:14][N+:15]([O-:17])=[O:16].O>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:9]([F:12])([F:11])[F:10])=[CH:14][N+:15]([O-:17])=[O:16])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6375NitromethaneHCID 6038664'-Bromo-2,2,2-trifluoroacetophenone

Product 1

HCID 536841792-(4-Bromophenyl)-3,3,3-trifluoronitropropene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred solution of 4′-bromo-2,2,2-trifluoroacetophenone (0.392 g, 2.00 mmol) and CH3NO2 (0.488 g, 8.0 mmol) in dry toluene (70 mL) containing N,N-diethylenediamine (30 mmol) is heated at reflux with a Dean and Stark trap until complete removal of H2O. The cooled solution is washed with 5% aqueous HCl, dried over MgSO4, filtered, evaporated in vacuo and the resulting residue when purified by chromatography gives the title compound.

Workup

  1. temperatureis heated
  2. washThe cooled solution is washed with 5% aqueous HCl
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customthe resulting residue when purified by chromatography

Sources & evidence

ORD record
ord-6e7c6eda8900428385b49fc10c46cf74
Source dataset
uspto-grants-2002_03
Patent number
US06358981B1

Reaction notes

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