Formaldehyde → 6-Bromo-5-fluoro-2-methylene-2,3-dihydro-1H-inden-1-one

HRID 1468080Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1468080
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:11])=[CH:4][C:3]=1[F:12].C=O.F[C:16](F)(F)C([O-])=O.C[NH2+]C1C=CC=CC=1>C1COCC1>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[CH2:16])[C:8]2=[O:11])=[CH:4][C:3]=1[F:12]

Komponenten

5

Edukt 3

HCID 712FormaldehydeHCID 2724109N-Methylanilinium trifluoroacetateHCID 198011566-Bromo-5-fluoro-2,3-dihydro-1H-inden-1-one

Produkt 1

HCID 867066926-Bromo-5-fluoro-2-methylene-2,3-dihydro-1H-inden-1-oneAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

6-Bromo-5-fluoro-2,3-dihydro-1H-inden-1-one (commercially available), 4 g, 17.5 mmol), paraformaldehyde (2.48 g, 78.6 mmol) and N-methylanilinium trifluoroacetate (5.79 g, 26.2 mmol) were dissolved in anhydrous THF (80 mL) and refluxed overnight. The mixture was cooled to r.t. and concentrated. The residue was re-dissolved in EtOAc and brine. The phases were separated and the organic phase was dried over sodium sulfate and concentrated. The product was purified by flash column chromatography using heptane/EtOAc 7:1 as eluent affording the title compound (2.99 g, 71% yield). 1H NMR (400 MHz, CDCl3) δ ppm 3.73 (s, 3 H) 5.69 (m, 1 H) 6.39 (m, 1 H) 7.25 (s, 2 H) 8.10 (d, 1 H); MS (EI) m/z 240, 242 M+.

Aufarbeitung

  1. temperaturerefluxed overnight
  2. concentrationconcentrated
  3. dissolutionThe residue was re-dissolved in EtOAc
  4. customThe phases were separated
  5. dry with materialthe organic phase was dried over sodium sulfate
  6. concentrationconcentrated
  7. customThe product was purified by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-57c38aa1a07946b3959790b4caa4d9fd
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09000183B2

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