Trifluoromethanesulfonic anhydride → HCID 89350907, Verbindung

HRID 1470513Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1470513
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10]([C:12](O)=[O:13])=[CH:9][CH:8]=[C:7]2[O:15]C.C[CH2:18][N:19]([CH:23](C)C)C(C)C.[O:26](S(C(F)(F)F)(=O)=O)[S:27]([C:30]([F:33])([F:32])[F:31])(=O)=[O:28]>C(Cl)Cl>[F:31][C:30]([F:33])([F:32])[S:27]([O:15][C:7]1[C:6]2[C:11](=[C:2]([Cl:1])[CH:3]=[CH:4][CH:5]=2)[C:10]([C:12](=[O:13])[N:19]([CH3:23])[CH3:18])=[CH:9][CH:8]=1)(=[O:28])=[O:26]

Komponenten

5

Edukt 3

HCID 67749Trifluoromethanesulfonic anhydrideHCID 81531DiisopropylethylamineHCID 71185803HCID 71185803, Verbindung

Produkt 1

HCID 89350907HCID 89350907, VerbindungAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a mixture of 8-chloro-4-methoxy-1-naphthoic acid (step-6 intermediate) (0.14 g, 0.561 mmol) in DCM (5 mL) was added, DIPEA (0.20 mL, 1.12 mmol) at 0° C. After 5 min stirring, Tf2O (0.11 mL, 0.67 mmol) was added to it. The resulting mixture was stirred for 2 h before quenching with ice water. The aqueous layer was extracted with DCM, and the combined organic layer was washed with, water, brine, dried over Na2SO4 and filtered. The solvent was removed under reduced pressure and the residue was purified by column chromatography to furnish the desired trifliate intermediate as a pale yellow oil (100 mg, 47%).

Aufarbeitung

  1. additionwas added
  2. customat 0° C
  3. stirringThe resulting mixture was stirred for 2 h
  4. custombefore quenching with ice water
  5. extractionThe aqueous layer was extracted with DCM
  6. washthe combined organic layer was washed with, water, brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customThe solvent was removed under reduced pressure
  10. customthe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c1cf468b6ce447bebd7c23c3d985c27e
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09006442B2

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