Boron trifluoride etherate → Dibenz[b,e]oxepin-11(6H)-one

HRID 718118

Reaktionsgleichung

Reaktionsgleichung von HRID 718118
[O:1]([CH2:8][C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([OH:13])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.B(F)(F)F.CCOCC>C(Cl)Cl>[CH:4]1[C:3]2[C:11](=[O:13])[C:10]3[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=3[CH2:8][O:1][C:2]=2[CH:7]=[CH:6][CH:5]=1

Komponenten

5

Edukt 3

HCID 8000Boron trifluoride etherateHCID 9845Trifluoroacetic anhydrideHCID 697612-(Phenoxymethyl)benzoic acid

Produkt 1

HCID 78259Dibenz[b,e]oxepin-11(6H)-oneAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

The 2-(phenoxymethyl)benzoic acid (22.18 g, 97 mmol) was dissolved in DCM (200 mL) and trifluoroacetic anhydride (20.59 mL, 146 mmol) was added, followed by a catalytic amount of borontrifluoride etherate (2.22 mL, 17.5 mmol). The reaction mixture was heated at 40° C. for 2 hours. The solution was then washed with water, sodium bicarbonate (saturated solution) and water. The organic phases was dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified on silica gel (10-20% ethyl acetate in hexanes) to afford title compound 482 (19.937 g, 98%) as a light pink solid. MS (m/z): 211.1 (M+H).

Aufarbeitung

  1. washThe solution was then washed with water, sodium bicarbonate (saturated solution) and water
  2. dry with materialThe organic phases was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified on silica gel (10-20% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-66b607ca772f4e40bce4652b7021ae2c
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09193749B2

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