Sodium Carbonate → 2-(Cyclopent-1-en-1-yl)-4-fluoro-1-methoxybenZene

HRID 383349

Reaktionsgleichung

Reaktionsgleichung von HRID 383349
Br[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[O:9][CH3:10].[C:11]1(B(O)O)[CH2:15][CH2:14][CH2:13][CH:12]=1.C([O-])([O-])=O.[Na+].[Na+]>C(#N)C.ClCCl.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:11]1([C:2]2[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=2[O:9][CH3:10])[CH2:15][CH2:14][CH2:13][CH:12]=1

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 1362922-Bromo-4-fluoroanisoleHCID 3861343(Cyclopent-1-en-1-yl)boronic acid

Produkt 1

HCID 593949342-(Cyclopent-1-en-1-yl)-4-fluoro-1-methoxybenZeneAusbeute 49,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 6342AcetonitrileLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A microwave vial was charged with 2-bromo-4-fluoro-1-methoxybenzene (500 mg, 2.44 mmol), 1-cyclopentenylboronic acid (273 mg, 2.44 mmol), and Pd(dppf)Cl2 (199 mg, 0.24 mmol). The solids were dissolved in acetonitrile (7 mL) and 2 M Na2CO3 (5 mL) and the mixture heated under microwave irradiation for 20 min at 110° C. The reaction was diluted with dichloromethane (50 mL) and the layers separated. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated. Purification by silica gel chromatography (10-30% ethyl acetate/hexane) provided 2-cyclopentenyl-4-fluoro-1-methoxybenzene (231 mg, 49% yield). 1H NMR (400.0 MHz, DMSO-d6) δ 7.01 (dd, J=3.1, 10.0 Hz, 1H), 6.92-6.82 (m, 1H), 6.54 (dd, J=2.4, 6.5 Hz, 1H), 6.54 (s, 1H), 3.87 (s, 3H), 2.78-2.73 (m, 2H), 2.62-2.57 (m, 2H), 2.03-1.95 (m, 2H).

Aufarbeitung

  1. customthe layers separated
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by silica gel chromatography (10-30% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-6f855cbf05f34ea5b1929c1c4412c1d3
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367660B2

Verknüpfte Notizen

Wird geladen…