Triethylamine → 4-Fluoro-2-(4-methanesulfonyl-phenylethynyl)-benzaldehyde

HRID 1644720Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1644720
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9]([CH3:12])(=[O:11])=[O:10])=[CH:5][CH:4]=1)#[CH:2].C(N(CC)CC)C.Br[C:21]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:22]=1[CH:23]=[O:24]>ClCCl.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.[Cu]I>[F:29][C:27]1[CH:28]=[CH:21][C:22]([CH:23]=[O:24])=[C:25]([C:2]#[C:1][C:3]2[CH:4]=[CH:5][C:6]([S:9]([CH3:12])(=[O:10])=[O:11])=[CH:7][CH:8]=2)[CH:26]=1

Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 27733192-Bromo-4-fluorobenzaldehydeHCID 220426121-Ethynyl-4-(methanesulfonyl)benzene

Produkt 1

HCID 593508304-Fluoro-2-(4-methanesulfonyl-phenylethynyl)-benzaldehydeAusbeute 79,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A degassed mixture of 1-ethynyl-4-methanesulfonyl-benzene (2.5 g, 13.87 mmol), bis(triphenylphosphine)palladium(II) chloride (0.49 g, 0.69 mmol), copper(I) iodide (0.13 g, 0.69 mmol), triethylamine (28 mL), and 2-bromo-4-fluorobenzaldehyde (3.38 g, 16 mmol) in dichloromethane (10 mL) was stirred at 80° C. for 3.5 hours, then at room temperature overnight. The reaction mixture was partitioned between dichloromethane and water. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (RediSep® Flash column, 230-400 mesh, 15-35% ethyl acetate in hexane) gave 4-fluoro-2-(4-methanesulfonyl-phenylethynyl)-benzaldehyde (3.32 g, 79%). MS (ESI+) cald. for C16H11FO3S [(M+H)+] 302, obsd. 302.

Aufarbeitung

  1. customat room temperature
  2. customovernight
  3. customThe reaction mixture was partitioned between dichloromethane and water
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5476d957c5804cba8b67c683dddda991
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08124629B2

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