Toluene → Methyl 2-(perfluoro-1-butanesulfonyloxy)-1-napthoate

HRID 430039

Reaktionsgleichung

Reaktionsgleichung von HRID 430039
[F:1][C:2]([F:17])([S:13](F)(=[O:15])=[O:14])[C:3]([F:12])([F:11])[C:4]([F:10])([F:9])[C:5]([F:8])([F:7])[F:6].[OH:18][C:19]1[CH:28]=[CH:27][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]=1[C:29]([O:31][CH3:32])=[O:30].C(N(CC)CC)C.C1(C)C=CC=CC=1>O1CCCC1>[F:1][C:2]([F:17])([S:13]([O:18][C:19]1[CH:28]=[CH:27][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]=1[C:29]([O:31][CH3:32])=[O:30])(=[O:15])=[O:14])[C:3]([F:12])([F:11])[C:4]([F:10])([F:9])[C:5]([F:8])([F:7])[F:6]

Komponenten

6

Edukt 4

HCID 1140TolueneHCID 8471TriethylamineHCID 67814Perfluoro-1-butanesulfonyl fluorideHCID 598533Methyl 2-hydroxy-1-naphthoate

Produkt 1

HCID 18353806Methyl 2-(perfluoro-1-butanesulfonyloxy)-1-napthoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Perfluoro-1-butanesulfonyl fluoride (19 mL, 106 mmol, 1 eq) was added to a solution of methyl 2-hydroxy-1-naphthoate (21.25 g, 105 mmol, 1 eq) and triethylamine (15 mL, 108 mmol, 1 eq) in tetrahydrofuran (150 mL) maintained at an internal temperature about 0° C., under nitrogen. Once the addition was complete, the mixture was allowed to warm to ambient temperature and stirred for 64 hours. Toluene (150 mL) was added causing some precipitation. The solids were removed by filtration through Celiteä and washed with toluene (20 mL). The organic solutions were combined and washed with 2 N HCl (aq) (2×50 mL), water (100 mL), saturated aqueous sodium carbonate solution (100 mL) and brine (100 mL). The organic layer was dried (MgSO4), filtered and concentrated under reduced pressure. Yield 48.79 g, 95%

Aufarbeitung

  1. additionOnce the addition
  2. temperatureto warm to ambient temperature
  3. customsome precipitation
  4. customThe solids were removed by filtration through Celiteä
  5. washwashed with toluene (20 mL)
  6. washwashed with 2 N HCl (aq) (2×50 mL), water (100 mL), saturated aqueous sodium carbonate solution (100 mL) and brine (100 mL)
  7. dry with materialThe organic layer was dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-0b6ac454dd9f4f31a52a4a5d6e0de927
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06320068B1

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