1,2-Dibromoethane → 7-Fluoro-5-nitro-2,3-dihydrobenzo[b][1,4]dioxine

HRID 2167731Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2167731
C([O-])([O-])=O.[K+].[K+].[F:7][C:8]1[CH:13]=[C:12]([OH:14])[C:11]([OH:15])=[C:10]([N+:16]([O-:18])=[O:17])[CH:9]=1.Br[CH2:20][CH2:21]Br>CN(C=O)C.C(OCC)(=O)C>[F:7][C:8]1[CH:9]=[C:10]([N+:16]([O-:18])=[O:17])[C:11]2[O:15][CH2:21][CH2:20][O:14][C:12]=2[CH:13]=1

Komponenten

6

Edukt 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 688163705-Fluoro-3-nitrobenzene-1,2-diol

Produkt 1

HCID 688171507-Fluoro-5-nitro-2,3-dihydrobenzo[b][1,4]dioxine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

K2CO3 (15.27 g, 110.6 mmol) was added to a solution of 5-fluoro-3-nitrobenzene-1,2-diol (5 g, 28.9 mmol) in DMF (35 mL) followed by the addition of 1,2-Dibromoethane (13.63 g, 6.25 mL, 72.5 mmol) and stirring was continued at 80° C. for 2 h. Reaction mixture was diluted with ethyl acetate, washed with cold water, dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford the crude, which was purified by MPLC (silica gel, Mobile Phase: ethyl acetate in n-Hexane 0 to 5% as eluant) to afford 7-fluoro-5-nitro-2,3-dihydrobenzo[b][1,4]dioxine (Int-51) as pale yellow solid. 1H NMR (300 MHz, CDCl3) δ ppm 7.3-7.2 (1H, dd), 6.9-6.8 (1H, dd), 4.4 (4H, s).

Aufarbeitung

  1. customReaction mixture
  2. washwashed with cold water
  3. dry with materialdried over anhydrous sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customto afford the crude, which
  6. customwas purified by MPLC (silica gel, Mobile Phase: ethyl acetate in n-Hexane 0 to 5% as eluant)

Quellen und Nachweise

ORD-Eintrag
ord-86495fda2f3741e191132791a323e774
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09045478B2

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