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

HRID 530673Notes

Reaction equation

HRID 530673 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9].[OH-].[Na+].[I-:14].[Na+].Cl[O-].[Na+].Cl>CO.[Cl-].[Na+].O>[I:14][C:7]1[CH:6]=[CH:5][C:4]([OH:9])=[C:3]([C:2]([F:10])([F:11])[F:1])[CH:8]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 14798Sodium HydroxideHCID 679582-TrifluoromethylphenolHCID 23665760Sodium Hypochlorite

Product 1

HCID 533389294-Iodo-2-(trifluoromethyl)phenol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of 2-trifluoromethylphenol (10 g, 61.7 mmol) in methanol (125 mL) at room temperature was treated with sodium hydroxide (13.87 g, 93 mmol) and stirred until homogeneous. The mixture was cooled in an ice bath and sodium iodide (2.96 g, 74 mmol) was added portionwise followed by the addition of 10% sodium hypochlorite (84 mL, 136 mmol) dropwise, dividing these reagents into 3 portions and adding them sequentially over 30 minutes. The solution was then adjusted to pH 1 by dropwise addition of concentrated hydrochloric acid and poured into brine. The product was extracted into ethyl acetate, concentrated in vacuo and purified by silica gel flash chromatography eluting with ethyl acetate/hexane (0% to 5%) to give the title compound.

Workup

  1. temperatureThe mixture was cooled in an ice bath
  2. additionadding them sequentially over 30 minutes
  3. extractionThe product was extracted into ethyl acetate
  4. concentrationconcentrated in vacuo
  5. custompurified by silica gel flash chromatography
  6. washeluting with ethyl acetate/hexane (0% to 5%)

Sources & evidence

ORD record
ord-2973be5a31f0440fbf15fe197cd825e2
Source dataset
uspto-grants-2016_05
Patent number
US09353091B2

Reaction notes

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