Selectfluor → Methyl 5-fluoro-6-hydroxynaphthalene-1-carboxylate

HRID 1925361Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1925361
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=[CH:5]2.[B-](F)(F)(F)[F:17].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1>C(#N)C.C(OCC)(=O)C>[F:17][C:3]1[C:2]([OH:1])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]([O:14][CH3:15])=[O:13]

Komponenten

5

Edukt 2

HCID 2724933SelectfluorHCID 11367671Methyl 6-hydroxy-1-naphthoate

Produkt 1

HCID 24823729Methyl 5-fluoro-6-hydroxynaphthalene-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

To a stirred solution of methyl 6-hydroxy-1-naphthoate (25 g, 123.8 mmol) in anhydrous acetonitrile (130 mL), SelectFluor (45 g, 127.5 mmol) was added and the reaction vessel sealed (sealed tube). The reaction mixture was heated to 85° C. for 3 d. The reaction mixture was allowed to cool to RT, diluted with ethyl acetate and washed with water, then brine, dried with Na2SO4, filtered and evaporated. The mixture was purified by column chromatography using methylene chloride as the eluent. The title compound was obtained as a tan solid.

Aufarbeitung

  1. customthe reaction vessel sealed
  2. custom(sealed tube)
  3. temperatureto cool to RT
  4. washwashed with water
  5. dry with materialbrine, dried with Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe mixture was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b43d0d7d09c1476f8bddcd14619abc56
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08178557B2

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