Hydrochloric Acid → 2-Iodo-5-(trifluoromethyl)phenol

HRID 391355Notes

Reaction equation

HRID 391355 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.[H-].[Na+].[I:14]I.Cl>C1(C)C=CC=CC=1>[I:14][C:6]1[CH:7]=[CH:8][C:3]([C:2]([F:10])([F:11])[F:1])=[CH:4][C:5]=1[OH:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 807IodineHCID 73763-(Trifluoromethyl)phenolHCID 24758Sodium hydride

Product 1

HCID 138235382-Iodo-5-(trifluoromethyl)phenolYield 104.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A toluene (200.0 mL) solution of 3-trifluoromethylphenol (16.6 g) was added dropwise to a toluene (300.0 mL) suspension of sodium hydride (7.1 g) under ice cooling. The reaction mixture was stirred at the same temperature for 30 minutes, and iodine (26.0 g) was then added thereto. The solution was stirred at room temperature for 12 hours. Subsequently, 3 N hydrochloric acid was added to the solution so that the pH of the solution was adjusted to 2. The solution was extracted with ethyl acetate. The organic layer was sequentially washed with water and a saturated brine and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The title crude compound (30.8 g) was obtained as pale yellow oil.

Workup

  1. stirringThe solution was stirred at room temperature for 12 hours
  2. extractionThe solution was extracted with ethyl acetate
  3. washThe organic layer was sequentially washed with water
  4. dry with materiala saturated brine and then dried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-655aa2ca60f5462db5af95d9edd24294
Source dataset
uspto-grants-2013_02
Patent number
US08383839B2

Reaction notes

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