Sodium Iodide → 2-Iodo-4-(trifluoromethyl)phenol
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
Product 1
Reagents, catalysts & solvents 2
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
- extractionextracted with ethylacetate
- washThe organic phase was washed with sodium thiosulfate solution
- dry with materialdried (MgSO4)
- concentrationconcentrated in vacuo
- customThe residue was purified by chromatography (silica, eluting with isohexane:ethyl acetate)
Sources & evidence
- ORD record
- ord-1e2552f608414f098ff5e79320e33a6d
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07737135B2
Reaction notes
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