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

HRID 221283

Reaktionsgleichung

Reaktionsgleichung von HRID 221283
[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]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 22292821N-trifluoroacetyl-2-iodo-4-chlorophenethylamineAusbeute 38,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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 to 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.

Aufarbeitung

  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 to with brine (50 mL)
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-fc81e168c0f642fda9f682723ed4c260
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08207158B2

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