Diethyl Ether → 4'-Nitro-3'-[2-(trifluoromethyl)phenylthio]acetophenone

HRID 1087186Notes

Reaction equation

HRID 1087186 reaction equation
Cl[C:2]1[CH:3]=[C:4]([C:11](=[O:13])[CH3:12])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[F:14][C:15]([F:24])([F:23])[C:16]1[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=1[S-:18].[Li+].CCOCC.C(OCC)(=O)C>C1(C)C=CC=CC=1.O>[N+:8]([C:7]1[CH:6]=[CH:5][C:4]([C:11](=[O:13])[CH3:12])=[CH:3][C:2]=1[S:18][C:17]1[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=1[C:15]([F:14])([F:23])[F:24])([O-:10])=[O:9]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 8857Ethyl AcetateHCID 104427551-(3-Chloro-4-nitrophenyl)ethanoneHCID 67871513Lithium 2-(trifluoromethyl)thiophenoxide

Product 1

HCID 102466754'-Nitro-3'-[2-(trifluoromethyl)phenylthio]acetophenone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A solution of 3'-chloro-4'-nitroacetophenone (2.7 g) in toluene (50 ml) was added to a stirred solution of lithium 2-(trifluoromethyl)thiophenoxide [4.4 g; Aust. J. Chem. 32 2313 (1979)]in ether (142 ml) at 0° C. The mixture was stirred at room temperature for 2 hours and refluxed for 20 minutes. The resulting mixtures were added ethyl acetate and water, and the organic layer was washed with water, dried and evaporated. The oily residue was purified by column chromatography on silica gel (70 g) eluting with toluene to give a yellow oil of 4'-nitro-3'-[2-(trifluoromethyl)phenylthio]acetophenone (1.3 g).

Workup

  1. customat 0° C
  2. temperaturerefluxed for 20 minutes
  3. washthe organic layer was washed with water
  4. customdried
  5. customevaporated
  6. customThe oily residue was purified by column chromatography on silica gel (70 g)
  7. washeluting with toluene

Sources & evidence

ORD record
ord-dc4702a2dac9434bb54d0b0ac3a1712f
Source dataset
uspto-grants-1991_07
Patent number
US05034417

Reaction notes

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