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

HRID 46306Notes

Reaction equation

HRID 46306 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 94%

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 room temperature under nitrogen for 48 hours before diluting with water and extracting with dichloromethane. Organic extract was washed with water, saturated aqueous sodium thiosulphate solution, water, dried over magnesium sulfate and decolourising 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 evaporated in vacuo to give the title compound as an oil, 8.78 g, 94% yield.

Workup

  1. extractionextracting with dichloromethane
  2. extractionOrganic extract
  3. washwas washed with water, saturated aqueous sodium thiosulphate solution, water
  4. dry with materialdried over 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. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-ed5b836a8b304d37a4e16c36dca41b8e
Source dataset
uspto-grants-2013_09
Patent number
US08541588B2

Reaction notes

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