Trifluoromethanesulfonic acid → N-trifluoroacetyl-2-iodo-4-chlorophenethylamine

HRID 84116

Reaction equation

HRID 84116 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

Reactant 3

HCID 62406Trifluoromethanesulfonic acidHCID 10883201Bis(pyridine)iodonium tetrafluoroborateHCID 22292794n-Trifluoroacetyl-4-chlorophenethylamine

Product 1

HCID 22292821N-trifluoroacetyl-2-iodo-4-chlorophenethylamineYield 38.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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

  1. concentrationThe product mixture was concentrated
  2. dissolutiondissolved in EtOAc (100 mL)
  3. washwashed twice with 5% aqueous sodium bisulfite (50 mL), twice with saturated aqueous NaHCO3, (50 mL) once with brine (50 mL)
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-cec1420d753248ff8235aef281b7638e
Source dataset
uspto-grants-2014_09
Patent number
US08846906B2

Linked notes

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