Sulfuric Acid → HCID 66652905, compound

HRID 2283628Notes

Reaction equation

HRID 2283628 reaction equation
S(=O)(=O)(O)O.[F:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][C:8]=1[C:14]([F:17])([F:16])[F:15].[I:18]N1C(=O)CCC1=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(O)(=O)C.O>[F:6][C:7]1[C:8]([C:14]([F:15])([F:16])[F:17])=[CH:9][C:10]([OH:13])=[C:11]([I:18])[CH:12]=1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 24477Sodium ThiosulfateHCID 120273N-Iodosuccinimide3×HCID 6018544-Fluoro-3-(trifluoromethyl)phenol

Product 1

HCID 66652905HCID 66652905, compoundYield 119.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Concentrated sulfuric acid (0.78 mL. 15.0 mmol) was added to a mixture of 4-fluoro-3-(trifluoromethyl)phenol (8.00 g, 44.4 mmol) and N-iodosuccinimide (5.00 g, 22.2 mmol) in acetic acid (40 mL) at 0° C. After 1 hour, the ice bath was removed and an additional portion of N-iodosuccinimide (1.50 g. 6.67 mmol) added. After an additional 1 hour at ambient temperature, the final portion of N-iodosuccinimide (1.0 g, 4.4 mmol) was added. The reaction mixture was stirred for 1 hour then diluted with water (300 mL), treated with 20 wt % aqueous sodium thiosulfate, and extracted with ether (3×100 mL). The combined organic layers were washed with aqueous sodium thiosulfate then brine, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by automated silica gel flash chromatography (100% hexanes to 50% dichloromethane in hexanes gradient elution) to afford the title compound as a yellow oil (8.1 g).

Workup

  1. customthe ice bath was removed
  2. waitAfter an additional 1 hour at ambient temperature
  3. extractionextracted with ether (3×100 mL)
  4. washThe combined organic layers were washed with aqueous sodium thiosulfate
  5. dry with materialbrine, dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by automated silica gel flash chromatography (100% hexanes to 50% dichloromethane in hexanes gradient elution)

Sources & evidence

ORD record
ord-398357a4b36a46f9a51c3fb37a9c11f4
Source dataset
uspto-grants-2015_09
Patent number
US09145407B2

Reaction notes

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