Hydroxy tosyloxy iodobenzene → alpha-(Acetyl)4-(trifluoromethyl)-2,6-dinitrobenzyl tosylate

HRID 355305Notes

Reaction equation

HRID 355305 reaction equation
[C:1]([CH2:4][C:5]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:8]([C:14]([F:17])([F:16])[F:15])=[CH:7][C:6]=1[N+:18]([O-:20])=[O:19])(=[O:3])[CH3:2].OC1C([O:29][S:30]([C:33]2[CH:39]=[CH:38][C:36]([CH3:37])=[CH:35][CH:34]=2)(=[O:32])=[O:31])=C(I)C=CC=1>>[S:30]([C:33]1[CH:39]=[CH:38][C:36]([CH3:37])=[CH:35][CH:34]=1)([O:32][CH:4]([C:1](=[O:3])[CH3:2])[C:5]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:8]([C:14]([F:16])([F:15])[F:17])=[CH:7][C:6]=1[N+:18]([O-:20])=[O:19])(=[O:31])=[O:29]

Participants

3

Reactant 2

HCID 21918218Hydroxy tosyloxy iodobenzeneHCID 22118157alpha-(Acetyl)4-(trifluoromethyl)-2,6-dinitrotoluene

Product 1

HCID 22118159alpha-(Acetyl)4-(trifluoromethyl)-2,6-dinitrobenzyl tosylateYield 25.3%

Procedure

α-(Acetyl)4-(trifluoromethyl)-2,6-dinitrotoluene (5.00 g, 17.10 mmol) was heated to 80° C. for 10 minutes under nitrogen. Hydroxy(tosyloxy) iodobenzene (13.40 g, 34.18 mmol) was then added slowly keeping the temperature constant at 80° C. The reaction mixture was allowed to stir for 1 hour, carefully avoiding overheating. After cooling, the reaction mixture was purified by column chromatography over silica gel (60-200 mesh) using CH2Cl2 /hexane (1:1) as the eluant. Recrystallization with chloroform/petroleum ether gave 2 g (25%) of pure product.

Workup

  1. customconstant at 80° C
  2. temperatureAfter cooling
  3. customthe reaction mixture was purified by column chromatography over silica gel (60-200 mesh)
  4. customRecrystallization with chloroform/petroleum ether

Sources & evidence

ORD record
ord-4a69676c2fc34d0fab8d71a18c5a6176
Source dataset
uspto-grants-1998_11
Patent number
US05830619

Reaction notes

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