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

HRID 2266138Notes

Reaction equation

HRID 2266138 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]

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 962WaterSolvent

Procedure

To a solution of 2-Isopropyl4-methoxy-1-(toluene4-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-Iodo4-isopropyl-2-methoxy-5-(toluene4-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-6ad332085dec4a4c8b150d0b417e5442
Source dataset
uspto-grants-2010_12
Patent number
US07858632B2

Reaction notes

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