Boron tribromide → N-Trifluoroacetyl-8-bromo-7-hydroxy-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine

HRID 84077Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 84077
[F:1][C:2]([F:21])([F:20])[C:3]([N:5]1[CH2:11][CH:10]([CH3:12])[C:9]2[CH:13]=[C:14]([Br:19])[C:15]([O:17]C)=[CH:16][C:8]=2[CH2:7][CH2:6]1)=[O:4].B(Br)(Br)Br>ClCCl>[F:20][C:2]([F:1])([F:21])[C:3]([N:5]1[CH2:11][CH:10]([CH3:12])[C:9]2[CH:13]=[C:14]([Br:19])[C:15]([OH:17])=[CH:16][C:8]=2[CH2:7][CH2:6]1)=[O:4]

Komponenten

4

Edukt 2

HCID 25134Boron tribromideHCID 22292777HCID 22292777, Verbindung

Produkt 1

HCID 22292819N-Trifluoroacetyl-8-bromo-7-hydroxy-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepineAusbeute 86,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of N-trifluoroacetyl-8-bromo-7-methoxy-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine (1.50 g, 4.10 mmol) in dichloromethane (80 mL) was treated dropwise with BBr3 (9.4 mL of a 1.0M solution in CH2Cl2, 9.4 mmol), and the mixture stirred overnight while warming to 20 C. The excess BBr3 was quenched with the dropwise addition of water, the mixture diluted with ether (200 mL), washed with Na2CO3 (100 mL) and brine (100 mL), dried with Na2SO4 and concentrated. Flash chromatography (15% EtOAc in hexane, silica) resulted in 1.25 g of a white solid foam.

Aufarbeitung

  1. temperaturewhile warming to 20 C
  2. customThe excess BBr3 was quenched with the dropwise addition of water
  3. additionthe mixture diluted with ether (200 mL)
  4. washwashed with Na2CO3 (100 mL) and brine (100 mL)
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-3319a59e6c5d46ba9ddf6caa388b54d4
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846906B2

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