Sodium Iodide → 2-Iodo-4-(trifluoromethyl)phenol

HRID 1023765Notes

Reaction equation

HRID 1023765 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.[Na+].[I-:13]>CN(C=O)C.Cl>[I:13][C:5]1[CH:4]=[C:3]([C:2]([F:10])([F:11])[F:1])[CH:8]=[CH:7][C:6]=1[OH:9]

Participants

5

Reactant 2

HCID 5238Sodium IodideHCID 678744-(Trifluoromethyl)phenol

Product 1

HCID 115728162-Iodo-4-(trifluoromethyl)phenolYield 91.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent

Procedure

4-(trifluoromethyl)-phenol (8 g) in anhydrous DMF (80 ml) was cooled to 0° C. NaI (9.06 g) and chloroamine-T (16.1 g) was added portionwise and stirred at room temperature overnight. Then diluted with 2M HCl and extracted with ethylacetate. The organic phase was washed with sodium thiosulfate solution, dried (MgSO4) and concentrated in vacuo. The residue was purified by chromatography (silica, eluting with isohexane:ethyl acetate) to give the sub-title compound as a yellow oil (13 g).

Workup

  1. extractionextracted with ethylacetate
  2. washThe organic phase was washed with sodium thiosulfate solution
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography (silica, eluting with isohexane:ethyl acetate)

Sources & evidence

ORD record
ord-0ea9f6bcb8e748fd9636101f8a4c5f0a
Source dataset
uspto-grants-2014_05
Patent number
US08722741B2

Reaction notes

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