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Iodine chloride → 1-Iodo-4-isopropyl-2-methoxy-5-(toluene-4-sulfonyl)-benzene

HRID 38394
Notes
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Reaction equation

HRID 38394 reaction equation
[CH:1]([C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:5]=1[S:12]([C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)(=[O:14])=[O:13])([CH3:3])[CH3:2].[I:22]Cl.C([O-])(O)=O.[Na+]>CC(O)=O.O>[I:22][C:7]1[CH:6]=[C:5]([S:12]([C:15]2[CH:16]=[CH:17][C:18]([CH3:21])=[CH:19][CH:20]=2)(=[O:13])=[O:14])[C:4]([CH:1]([CH3:3])[CH3:2])=[CH:9][C:8]=1[O:10][CH3:11]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 24640Iodine chlorideHCID 516892Sodium BicarbonateHCID 670535032-Isopropyl-4-methoxy-1-(toluene-4-sulfonyl)-benzene

Product 1

HCID 670534521-Iodo-4-isopropyl-2-methoxy-5-(toluene-4-sulfonyl)-benzeneYield 91.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×
HCID 962
Water
Solvent

Procedure

To a solution of 2-Isopropyl-4-methoxy-1-(toluene-4-sulfonyl)-benzene (10 g, 31.25 mmol) in HOAc (10 ml) was added a solution of ICl (9.6 g, 59.26 mmol) in HOAc (10 ml) and H2O (5 ml). The reaction mixture was stirred at room temperature for 16 hrs and basified by saturated NaHCO3 solution. The aqueous solution was extracted into EtOAc which was washed with water, brine, dried over Na2SO4, filtered and concentrated in vacuo to give 1-Iodo-4-isopropyl-2-methoxy-5-(toluene-4-sulfonyl)-benzene (12.35 g, 89%).

Workup

  1. extractionThe aqueous solution was extracted into EtOAc which
  2. washwas washed with water, brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bf078cc3500549939cc948b0ca729321
Source dataset
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08524725B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes