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

HRID 1694691Notes

Reaction equation

HRID 1694691 reaction equation
[I-:1].[Na+].CC1C=CC(S(NCl)(=O)=O)=CC=1.[F:15][C:16]([F:25])([F:24])[C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1>CN(C=O)C.Cl>[I:1][C:19]1[CH:18]=[C:17]([C:16]([F:24])([F:25])[F:15])[CH:22]=[CH:21][C:20]=1[OH:23]

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 31388TosylchloramideHCID 678744-(Trifluoromethyl)phenol

Product 1

HCID 115728162-Iodo-4-(trifluoromethyl)phenol

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium iodide (3.32 g) then chloramine-T (5.91 g) were added to a stirred solution of 4-trifluoromethylphenol (3.0 g) in DMF (30 ml) at O° C. The mixture was warmed to RT, stirred for 1 h, diluted with dilute hydrochloric acid then extracted with diethylether. The organic layer was washed with aqueous sodium thiosulphate solution, dried and the solvent removed under reduced pressure. Yield 5.25 g

Workup

  1. extractionthen extracted with diethylether
  2. washThe organic layer was washed with aqueous sodium thiosulphate solution
  3. customdried
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-4e0ca330737341b2bc1f05502f9f2977
Source dataset
uspto-grants-2012_04
Patent number
US08158820B2

Reaction notes

Loading…