Bromine → HCID 16100372, Verbindung

HRID 1424579Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1424579
BrBr.[Br-:3].[Al+3].[Br-:5].[Br-].[CH:7]12[CH2:16][CH:11]3[CH2:12][CH:13]([CH2:15][CH:9]([CH2:10]3)[CH:8]1[NH:17][C:18](=[O:20])[CH3:19])[CH2:14]2.S(=O)(O)[O-].[Na+]>C(Cl)Cl>[Br:3][C:11]12[CH2:16][CH:7]3[CH2:14][C:13]([Br:5])([CH2:15][CH:9]([CH:8]3[NH:17][C:18](=[O:20])[CH3:19])[CH2:10]1)[CH2:12]2

Komponenten

6

Edukt 4

HCID 24408BromineHCID 64498HCID 64498, VerbindungHCID 166749BromhydrolHCID 23665763Sodium Bisulfite

Produkt 1

HCID 16100372HCID 16100372, VerbindungAusbeute 28,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To bromine (20 mL, 40 mmol) and aluminum bromide (3.2 g, 20 mmol) was added N-(2-adamantyl)acetamide (4 g, 20 mmol) in portions. The reaction mixture was heated to 90° C. and stirred overnight. The mixture was cooled to rt and poured into ice/water. Satd aq sodium bisulfite was added slowly followed by dilution with CH2Cl2. The organic layer was separated, washed with brine, dried, filtered and concentrated. The crude product was purified by column chromatography to afford N-(5,7-dibromo-2-adamantyl)acetamide (1.98 g, 28%).

Aufarbeitung

  1. temperatureThe mixture was cooled to rt
  2. customThe organic layer was separated
  3. washwashed with brine
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-a123b8d7cca5420693a43676e6190de1
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08927715B2

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