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Water → 1-Isopropyl-5-methoxy-2-(toluene-4-sulfonyl)-4-trifluoromethyl-benzene

HRID 81810
Notes
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Reaction equation

HRID 81810 reaction equation
I[C:2]1[CH:7]=[C:6]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)(=[O:10])=[O:9])[C:5]([CH:18]([CH3:20])[CH3:19])=[CH:4][C:3]=1[O:21][CH3:22].[F-].[K+].[F:25][C:26](I)([F:28])[F:27].O>CN(C=O)C.[Cu]I>[CH:18]([C:5]1[CH:4]=[C:3]([O:21][CH3:22])[C:2]([C:26]([F:28])([F:27])[F:25])=[CH:7][C:6]=1[S:8]([C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=1)(=[O:10])=[O:9])([CH3:20])[CH3:19]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 16843TrifluoroiodomethaneHCID 522689Potassium FluorideHCID 670534521-Iodo-4-isopropyl-2-methoxy-5-(toluene-4-sulfonyl)-benzene

Product 1

HCID 670534811-Isopropyl-5-methoxy-2-(toluene-4-sulfonyl)-4-trifluoromethyl-benzeneYield 107.9%

Reagents, catalysts & solvents 2

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Catalyst
HCID 6228DimethylformamideSolvent

Procedure

To a hot mixture of 1-Iodo-4-isopropyl-2-methoxy-5-(toluene-4-sulfonyl)-benzene (0.5 g, 1.12 mmol), CuI, KF in anhydrous DMF (10 ml) at 120° C. oil bath temperature, was added trifluoromethyl iodide (0.64 g, 4.48 mmol) in portions over 30 min. The reaction mixture was heated for 4 hrs and poured into H2O (100 ml). The insoluble solid, which was collected by filtration was triturated with methylene chloride, filtered and concentrated to give 1-Isopropyl-5-methoxy-2-(toluene-4-sulfonyl)-4-trifluoromethyl-benzene (0.45 g, 100%) as a solid.

Workup

  1. temperatureThe reaction mixture was heated for 4 hrs
  2. filtrationThe insoluble solid, which was collected by filtration
  3. customwas triturated with methylene chloride
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-32ee993b2ce6444b8cac3160215421e4
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08846705B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes