Hydrochloric Acid → 1-Chloro-5-methyl-3,3-bis(trifluoromethyl)-1,3-dihydro-1lambda3,2-benziodoxole

HRID 926924Notes

Reaction equation

HRID 926924 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]([C:9]1[CH:14]=[C:13]([CH3:15])[CH:12]=[CH:11][C:10]=1[I:16])([OH:8])[C:4]([F:7])([F:6])[F:5].[ClH:19].Cl[O-].[Na+]>CC(O)C>[Cl:19][I:16]1[C:10]2[CH:11]=[CH:12][C:13]([CH3:15])=[CH:14][C:9]=2[C:3]([C:4]([F:7])([F:6])[F:5])([C:2]([F:1])([F:17])[F:18])[O:8]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3295551,1,1,3,3,3-hexafluoro-2-(2-iodo-5-methylphenyl)propan-2-olHCID 23665760Sodium Hypochlorite

Product 1

HCID 3269341-Chloro-5-methyl-3,3-bis(trifluoromethyl)-1,3-dihydro-1lambda3,2-benziodoxoleYield 76%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Compound 2 (60 mg, 156 μmol) was dissolved in 2 mL propan-2-ol, 10 μL hydrochloric acid (37%) and 50 μL sodium hypochlorite solution (10-15% in water) were added. A white precipitate appeared instantaneously. The reaction mixture was stirred 5 min at room temperature. The solvent was removed under vacuum and the residue was purified over silica gel column using dichloromethane as eluant to give 50 mg (119 μmol, 76% yield) of a white solid.

Workup

  1. customThe solvent was removed under vacuum
  2. customthe residue was purified over silica gel column

Sources & evidence

ORD record
ord-bdd966190639445a96b638c0a40f7f5e
Source dataset
uspto-grants-2016_03
Patent number
US09290421B2

Reaction notes

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