Trifluoromethanesulfonic acid → N-trifluoroacetyl-2-iodo-4-chlorophenethylamine
Reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]([NH:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)=[O:4].[B-](F)(F)(F)F.C1C=CN=CC=1.C1C=CN=CC=1.[IH2+:34].C(S(O)(=O)=O)(F)(F)F>ClCCl>[F:16][C:2]([F:1])([F:15])[C:3]([NH:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=1[I:34])=[O:4]Participants
5
Procedure
A solution of N-trifluoroacetyl-4-chlorophenethylamine (1.6 g, 6.4 mmol) in dichloromethane (20 mL) was treated with bis(pyridine)iodonium(I)tetrafluoroborate (2.6 g, 7.0 mmol), CF3SO3H (2.1 g, 14.1 mmol) and stirred overnight at 20 C. The product mixture was concentrated, dissolved in EtOAc (100 mL), washed twice with 5% aqueous sodium bisulfite (50 mL), twice with saturated aqueous NaHCO3, (50 mL) once with brine (50 mL), dried with Na2SO4 and concentrated to give 0.94 g of a clear oil. MS calculated for C10H8ClF3INO+H: 378, observed: 378.
Workup
- concentrationThe product mixture was concentrated
- dissolutiondissolved in EtOAc (100 mL)
- washwashed twice with 5% aqueous sodium bisulfite (50 mL), twice with saturated aqueous NaHCO3, (50 mL) once with brine (50 mL)
- dry with materialdried with Na2SO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-d79b2cbb27194322b8af050c41106bea
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08575149B2
Reaction notes
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