Cesium fluoride → HCID 13415926, Verbindung

HRID 2043317Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2043317
Br[CH:2]=[C:3]1[O:7][C:6](=[O:8])[CH:5]=[CH:4]1.[F:9][C:10]([F:21])([F:20])[C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.[F-].[Cs+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1.O.[Cl-].[Na+].O.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>[F:9][C:10]([F:21])([F:20])[C:11]1[CH:16]=[CH:15][C:14](/[CH:2]=[C:3]2/[CH:4]=[CH:5][C:6](=[O:8])[O:7]/2)=[CH:13][CH:12]=1

Komponenten

9

Edukt 3

HCID 25953Cesium fluorideHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 672283605-(Bromomethylidene)furan-2(5H)-one

Produkt 1

HCID 13415926HCID 13415926, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

A mixture containing 5-bromomethylene-2(5H)furanone (0.175 g, 1 mmol), 4-trifluoromethylphenylboronic acid (0.228 g, 1.2 mmol), trans-dichlorobis(triphenylphosphine)palladium (II) (0.035 g, 0.05 mmol), tetrabutylammonium iodide (0.018 g, 0.05 mmol) and cesium fluoride (0.456 g, 3 mmol) in toluene (10 mL) and water (10 mL) were stirred at reflux for 24 hours under nitrogen. After cooling, brine (50 mL) was added and the product extracted with ethyl acetate (50 mL×3). The organic fractions were combined, washed with brine (50 mL×3), dried over anhydrous sodium sulfate and evaporated to dryness to give a brown solid. The resulting solid was chromatographed (silica gel: eluent 50:50 dichloromethane/light petroleum) giving the desired product 29 as a light yellow powder. Yield 0.133 g (55%), m.p. 92-94° C., UV-Vis λmax (MeOH) 223 (15948), 237 (10856), 323(35739) nm. 1H NMR (CDCl3) δ 7.87 (d, J=8.3 Hz, 2H, H2′ and H6′), 7.63 (d, J=8.3 Hz, 2H, H3′ and H5′), 7.52 (d, J=5.7 Hz, 1H, H4), 6.28 (d, J=4.9 Hz, 1H, H3), 6.04 (s, 1H, H6).

Aufarbeitung

  1. temperatureat reflux for 24 hours under nitrogen
  2. temperatureAfter cooling
  3. extractionthe product extracted with ethyl acetate (50 mL×3)
  4. washwashed with brine (50 mL×3)
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated to dryness
  7. customto give a brown solid
  8. customThe resulting solid was chromatographed (silica gel: eluent 50:50 dichloromethane/light petroleum)

Quellen und Nachweise

ORD-Eintrag
ord-74f6e587eda54afe91a298bd3ffc4d55
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08586618B2

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