Water → HCID 46314739, Verbindung

HRID 659124Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 659124
Br[C:2]1[CH:3]=[CH:4][C:5]([F:10])=[C:6]([CH:9]=1)[C:7]#[N:8].[C:11]1(B(O)O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C([O-])([O-])=O.[Cs+].[Cs+].O>C1(C)C=CC=CC=1>[F:10][C:5]1[CH:4]=[CH:3][C:2]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:9][C:6]=1[C:7]#[N:8]

Komponenten

6

Edukt 4

HCID 962WaterHCID 10796Cesium carbonateHCID 66827Phenylboronic AcidHCID 27249005-Bromo-2-fluorobenzonitrile

Produkt 1

HCID 46314739HCID 46314739, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

5-Bromo-2-fluorobenzonitrile (53) (500 mg, 2.54 mmol) was coupled to phenylboronic acid (335 mg, 2.75 mmol) with Cs2CO3 (1.63 g, 5.00 mmol) in toluene (4 mL) in a microwave at 140° C. for 30 minutes. Water was added and the organics extracted several times with EtOAc, dried (MgSO4), filtered and the solvent concentrated in vacuo. The crude product was purified by Flash Master Jones Chromatography using a 25 g silica cartridge and eluting with 10% EtOAc in heptane to yield the title compound. Yield: 375 mg, 76%; LC-MS tr 1.63 min; HPLC Purity: 97%; MS (ES+) m/z not detectable (M+H)

Aufarbeitung

  1. dry with materialthe organics extracted several times with EtOAc, dried (MgSO4)
  2. filtrationfiltered
  3. concentrationthe solvent concentrated in vacuo
  4. customThe crude product was purified by Flash Master Jones Chromatography
  5. washeluting with 10% EtOAc in heptane

Quellen und Nachweise

ORD-Eintrag
ord-7bce9bd8947944bfb775552980f3b2a4
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08080567B2

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