Boron tribromide → 1-Chloro-7-fluoroisoquinolin-4-OL

HRID 1852218Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1852218
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([F:12])[CH:10]=2)[C:5]([O:13]C)=[CH:4][N:3]=1.B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([F:12])[CH:10]=2)[C:5]([OH:13])=[CH:4][N:3]=1

Komponenten

4

Edukt 2

HCID 25134Boron tribromideHCID 222502381-Chloro-7-fluoro-4-methoxyisoquinoline

Produkt 1

HCID 717427161-Chloro-7-fluoroisoquinolin-4-OLAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 1-chloro-7-fluoro-4-methoxyisoquinoline (0.75 g, 3.54 mmol) in DCM (10 ml) was added BBr3 (6.22 g, 24.81 mmol) at 0° C. drop wise. The reaction mass was refluxed for 5 h. The residue was cooled and quenched with methanol. The solvent was evaporated under reduced pressure and the residue was diluted with cold water. The precipitated solid was filtered, washed with water to get crude compound (0.65 g, 93%) as a pale yellow solid. 1H NMR (400 MHz, CD3OD): δ ppm 8.36-8.33 (m, 1H), 7.89-7.86 (d, J=12 Hz, 1H), 7.76 (s, 1H), 7.64 (t, J=10 Hz, 1H); MS: MS m/z 198.0 (M++1).

Aufarbeitung

  1. temperatureThe reaction mass was refluxed for 5 h
  2. temperatureThe residue was cooled
  3. customquenched with methanol
  4. customThe solvent was evaporated under reduced pressure
  5. additionthe residue was diluted with cold water
  6. filtrationThe precipitated solid was filtered
  7. washwashed with water

Quellen und Nachweise

ORD-Eintrag
ord-160f48e4fea6431fb1b19894e3a53384
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08957203B2

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