Boron tribromide → HCID 57894169, Verbindung

HRID 1822303Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1822303
[CH2:1]([O:3][C:4](=[O:24])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:19]=[C:18]([O:20]C)[CH:17]=[C:16]([F:22])[CH:15]=2)=[CH:9][C:8]=1[CH3:23])[CH3:2].B(Br)(Br)Br>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:24])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:19]=[C:18]([OH:20])[CH:17]=[C:16]([F:22])[CH:15]=2)=[CH:9][C:8]=1[CH3:23])[CH3:2]

Komponenten

4

Edukt 2

HCID 25134Boron tribromideHCID 57894216HCID 57894216, Verbindung

Produkt 1

HCID 57894169HCID 57894169, VerbindungAusbeute 81,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A −78° C. solution of 3-[4-(3-fluoro-5-methoxy-phenoxy)-2-methyl-phenyl]-propionic acid ethyl ester (0.715 g, 2.15 mmol) in dry CH2Cl2 (10 mL) is treated with a 1 M CH2Cl2 solution of boron tribromide (6.5 mL, 6.5 mmol). The mixture is warmed to 0° C. and stirred for 1 hour under N2. Upon completion, the mixture is poured into ice water and extracted with Et2O. The organic layer is dried (Na2SO4), and the solvent is removed in vacuo to afford crude product that is absorbed on silica gel and purified by flash chromatography using a gradient of 5/1 to 1/1 to hexanes/ethyl acetate to afford 0.558 g (81%) of the title compound. Rf=0.36 (2/1 hexanes/EtOAc). 1H NMR (400 MHz, CDCl3). MS (ES−) m/z mass calculated for C18H19O4F 318, found 317 (M−1, 100%).

Aufarbeitung

  1. extractionextracted with Et2O
  2. dry with materialThe organic layer is dried (Na2SO4)
  3. customthe solvent is removed in vacuo
  4. customto afford crude product that
  5. customis absorbed on silica gel
  6. custompurified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-5bb0fdceeec84eecb0d1953dfb5fc5e7
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07608639B2

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