Triethylamine → [4-fluoro-2-[(E)-2-(4-fluorophenyl)ethenyl]phenyl]methanol

HRID 514489Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 514489
Br[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][OH:10].[F:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]=[CH2:19])=[CH:14][CH:13]=1.CCN(CC)CC>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CN(C=O)C>[F:8][C:6]1[CH:5]=[CH:4][C:3]([CH2:9][OH:10])=[C:2](/[CH:19]=[CH:18]/[C:15]2[CH:16]=[CH:17][C:12]([F:11])=[CH:13][CH:14]=2)[CH:7]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 678834-FluorostyreneHCID 2773347(2-Bromo-4-fluorophenyl)methanol

Produkt 1

HCID 86725608[4-fluoro-2-[(E)-2-(4-fluorophenyl)ethenyl]phenyl]methanolAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

Charged (2-bromo-4-fluorophenyl)methanol (954 mg, 4.65 mmol), 4-fluoro-1-vinylbenzene (1.14 g, 9.31 mmol), Pd(PPh3)2Cl2 (49 mg, 0.07 mmol), Et3N (942 mg, 9.31 mmol) and DMF (5 mL) to a sealed tube, the mixture was then purged with nitrogen, heated to 150° C. for 3 h in microwave oven. The reaction mixture was filtered, the filtrate was then extracted with ethyl acetate, concentrated and purified by flash column chromatograph to give 569 mg of the title compound (50%). 1H NMR (400 MHz, CDCl3): δ 1.60 (1H, t, J=6.4 Hz), 4.78 (2H, d, J=6.4 Hz), 6.93-7.08 (4H, m), 7.31-7.35 (3H, m), 7.48-7.52 (2H, m).

Aufarbeitung

  1. customthe mixture was then purged with nitrogen
  2. filtrationThe reaction mixture was filtered
  3. extractionthe filtrate was then extracted with ethyl acetate
  4. concentrationconcentrated
  5. custompurified by flash column chromatograph

Quellen und Nachweise

ORD-Eintrag
ord-470cf675cae64eb1bbf473bbe2a1cd1d
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09107916B2

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