N-bromobutanimide → methyl 6-bromo-7-fluoro-2,2-dimethyl-3,4-dihydro-2H-chromene-4-carboxylate

HRID 510601Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 510601
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]([C:14]([O:16][CH3:17])=[O:15])[CH2:7][C:8]([CH3:13])([CH3:12])[O:9]2)=[CH:4][CH:3]=1.[Br:18]N1C(=O)CCC1=O>CN(C=O)C.C(OCC)(=O)C>[Br:18][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:2]=1[F:1])[O:9][C:8]([CH3:13])([CH3:12])[CH2:7][CH:6]2[C:14]([O:16][CH3:17])=[O:15]

Komponenten

5

Edukt 2

HCID 67184N-bromobutanimideHCID 67080255HCID 67080255, Verbindung

Produkt 1

HCID 67080243methyl 6-bromo-7-fluoro-2,2-dimethyl-3,4-dihydro-2H-chromene-4-carboxylateAusbeute 93,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Methyl 7-fluoro-2,2-dimethyl-3,4-dihydro-2H-chromene-4-carboxylate (187 mg, 0.785 mmol) was diluted with DMF (5 mL) followed by the addition of N-bromosuccinimide (154 mg, 0.863 mmol). The reaction was heated at 50° C. for 2.5 hours. The reaction was cooled, diluted with ethyl acetate and washed with water, saturated sodium bicarbonate, water, and brine. The organic layer was dried over MgSO4, filtered and concentrated. The material was purified using a Biotage 40M cartridge, gradient 5% ethyl acetate/hexane to 50% to yield the title compound (232 mg, 93.2% yield).

Aufarbeitung

  1. temperatureThe reaction was cooled
  2. washwashed with water, saturated sodium bicarbonate, water, and brine
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe material was purified

Quellen und Nachweise

ORD-Eintrag
ord-43a8351c3dd04aadacb70902337a17bb
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096567B2

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