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

HRID 46304

Reaction equation

HRID 46304 reaction equation
[I:1]N1C(=O)CCC1=O.[F:9][C:10]([F:19])([F:18])[C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1.S(=O)(=O)(O)O>C(O)(=O)C.O>[I:1][C:13]1[CH:12]=[C:11]([C:10]([F:18])([F:19])[F:9])[CH:16]=[CH:15][C:14]=1[OH:17]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 678744-(Trifluoromethyl)phenolHCID 120273N-Iodosuccinimide

Product 1

HCID 115728162-Iodo-4-(trifluoromethyl)phenolYield 63%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a suspension of N-iodosuccinimide (11.10 g, 49.5 mmol) in glacial acetic acid (40 ml) was added 4-trifluoromethyl phenol (8.02 g, 49.5 mmol) and, after 5 minutes, concentrated sulphuric acid (0.87 ml, 14.8 mmol). The pale brown/red suspension was stirred at room temperature under nitrogen for 48 hours before diluting with water and extracting with dichloromethane. The organic extract was washed with water, saturated aqueous sodium thiosulphate solution, water, dried over magnesium sulphate before decolourising charcoal added. The suspension was left to stand for 10 minutes before filtering through a short pad of silica gel eluting with dichloromethane. The solvent was evaporated in vacuo to give an oil which was purified by flash column chromatography on silica eluting with dichloromethane to give the title compound as a pale yellow oil, 9.017 g, 63% yield.

Workup

  1. extractionextracting with dichloromethane
  2. extractionThe organic extract
  3. washwas washed with water, saturated aqueous sodium thiosulphate solution, water
  4. dry with materialdried over magnesium sulphate
  5. additionadded
  6. waitThe suspension was left
  7. waitto stand for 10 minutes
  8. filtrationbefore filtering through a short pad of silica gel eluting with dichloromethane
  9. customThe solvent was evaporated in vacuo
  10. customto give an oil which
  11. customwas purified by flash column chromatography on silica eluting with dichloromethane

Sources & evidence

ORD record
ord-63a64ba6d2f3459284dce01856af67e8
Source dataset
uspto-grants-2013_09
Patent number
US08541588B2

Linked notes

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