Trifluoromethanesulfonic anhydride → Trifluoro-methanesulfonic acid 2-chloro-4-isopropyl-phenyl ester

HRID 2264986Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2264986
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].[Cl:16][C:17]1[CH:22]=[C:21]([CH:23]([CH3:25])[CH3:24])[CH:20]=[CH:19][C:18]=1O>C(Cl)Cl.N1C=CC=CC=1>[Cl:16][C:17]1[CH:22]=[C:21]([CH:23]([CH3:25])[CH3:24])[CH:20]=[CH:19][C:18]=1[O:6][S:3]([C:2]([F:15])([F:14])[F:1])(=[O:5])=[O:4]

Komponenten

5

Edukt 2

HCID 67749Trifluoromethanesulfonic anhydrideHCID 126520992-Chloro-4-isopropylphenol

Produkt 1

HCID 59596633Trifluoro-methanesulfonic acid 2-chloro-4-isopropyl-phenyl esterAusbeute 78,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

Trifluoromethanesulfonic anhydride (2.14 g, 7.6 mmol) was dissolved in DCM (5 ml) and cooled to 5° C. To this was added 2-chloro-4-isopropyl-phenol (1.23 g, 7.2 mmol), in 10 ml DCM and 1.75 ml pyridine, dropwise. The reaction mixture was stirred at 110° C. for 2 hours. The resultant dark solution was washed with 1M HCl (20 ml), water (20 ml) and saturated aqueous NaHCO3 (20 ml). The DCM extract was dried and concentrated in vacuo to provide the title compound as a dark orange oil (1.71 g, 78%). 1H NMR (CDCl3) 1.22-1.29 (6H, d, J=6.87 Hz), 2.88-3.00 (1H, sept, J=6.89 Hz), 7.15-7.20 (1H, m), 7.24 (1H, d, J=8.36 Hz), 7.36 (1H, d, J=2.17 Hz).

Aufarbeitung

  1. washThe resultant dark solution was washed with 1M HCl (20 ml), water (20 ml) and saturated aqueous NaHCO3 (20 ml)
  2. extractionThe DCM extract
  3. customwas dried
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6366ad55bd634365b777a553a5a9c55b
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07855216B2

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