Bromine → 3-Bromo-7-phenyl-hexahydroazepin-2-one

HRID 1271470Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1271470
P(Cl)(Cl)(Cl)(Cl)Cl.[C:7]1([CH:13]2[NH:19][C:18](=[O:20])[CH2:17][CH2:16][CH2:15][CH2:14]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[Br:21]Br>ClCCl.II>[Br:21][CH:17]1[CH2:16][CH2:15][CH2:14][CH:13]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:19][C:18]1=[O:20]

Komponenten

6

Edukt 3

HCID 24408BromineHCID 24819Phosphorus pentachlorideHCID 105595527-Phenylazepan-2-one

Produkt 1

HCID 140034323-Bromo-7-phenyl-hexahydroazepin-2-oneAusbeute 76,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 807IodineKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Phosphorus pentachloride (4.95 g, 23.8 mmol) was added to a solution of 7-phenylazepan-2-one (4.50 g, 23.8 mmol) in dichloromethane (75 mL) at 0° C. After 1 h, iodine (0.060 g, 0.24 mmol) and a solution of bromine (1.22 mL, 23.8 mmol) in dichloromethane (10 mL) were added sequentially and the mixture was allowed to warm to ambient temperature. After 1.5 h, the reaction was quenched with aqueous sodium sulfite. The mixture was extracted with dichloromethane (3×), and the combined organic extracts were dried over magnesium sulfate, filtered, and concentrated. Purification by silica gel chromatography (10% ethyl acetate/hexanes→50% ethyl acetate/hexanes) gave the title compound (4.91 g). MS 268 (M+1).

Aufarbeitung

  1. waitAfter 1.5 h
  2. customthe reaction was quenched with aqueous sodium sulfite
  3. extractionThe mixture was extracted with dichloromethane (3×)
  4. dry with materialthe combined organic extracts were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by silica gel chromatography (10% ethyl acetate/hexanes→50% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-d831491effd2476da890585cd5680b36
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07205292B2

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