Sulfuric Acid → 2-Iodo-4-(trifluoromethoxy)phenol

HRID 2283644Notes

Reaction equation

HRID 2283644 reaction equation
[I:1]N1C(=O)CCC1=O.[F:9][C:10]([F:20])([F:19])[O:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1.S(=O)(=O)(O)O>C(O)(=O)C.O>[I:1][C:14]1[CH:13]=[C:12]([O:11][C:10]([F:19])([F:20])[F:9])[CH:17]=[CH:16][C:15]=1[OH:18]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 70015p-(Trifluoromethoxy)phenolHCID 120273N-Iodosuccinimide

Product 1

HCID 27694112-Iodo-4-(trifluoromethoxy)phenolYield 12.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a suspension of N-iodosuccinimide (6.95 g, 31 mmol) in glacial acetic acid (2 ml) was added 4-trifluoromethoxy phenol (4.0 ml, 31 mmol) and, after 5 minutes, concentrated sulphuric acid (0.5 ml, 9 mmol). The pale brown suspension was stirred at ambient temperature under nitrogen for 48 hours before diluting with water and extracting with dichloromethane. The organic extract was washed with water, saturated aqueous sodium thiosulfate solution and water, dried over anhydrous magnesium sulfate and decolorizing charcoal added. The resulting suspension was left to stand for 30 minutes before filtering through a short pad of silica gel eluting with dichloromethane. The solvent was concentrated in vacuo to afford the title compound as an oil (1.18 g, 12%).

Workup

  1. extractionextracting with dichloromethane
  2. extractionThe organic extract
  3. washwas washed with water, saturated aqueous sodium thiosulfate solution and water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. additionadded
  6. waitThe resulting suspension was left
  7. waitto stand for 30 minutes
  8. filtrationbefore filtering through a short pad of silica gel eluting with dichloromethane
  9. concentrationThe solvent was concentrated in vacuo

Sources & evidence

ORD record
ord-91c7a348e0364a6aa9b271a418c93979
Source dataset
uspto-grants-2015_09
Patent number
US09145407B2

Reaction notes

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