Boron tribromide → HCID 86583544, Verbindung

HRID 1016774Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1016774
B(Br)(Br)Br.[C:5]([C:7]1[CH:12]=[CH:11][C:10]([NH:13][CH:14]([C:20]2[CH:25]=[CH:24][C:23]([O:26]C)=[C:22]([S:28][CH3:29])[CH:21]=2)[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:9][CH:8]=1)#[N:6]>C(Cl)Cl>[C:5]([C:7]1[CH:12]=[CH:11][C:10]([NH:13][CH:14]([C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[C:22]([S:28][CH3:29])[CH:21]=2)[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:9][CH:8]=1)#[N:6]

Komponenten

4

Edukt 2

HCID 25134Boron tribromideHCID 86583545HCID 86583545, Verbindung

Produkt 1

HCID 86583544HCID 86583544, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A 1M solution of BBr3 in CH2Cl2 (4.5 ml, 4.5 mmol) was added at −78° C. to a solution of the ethyl (RS)-(4-cyano-phenylamino)-(4-methoxy-3-methylsulphanyl-phenyl)-acetate (320 mg, 0.899 mmol) obtained in Example 167.2 in CH2Cl2 (10 ml). The mixture was stirred at −78° C. for 5 min., at 0° C. for 30 min. and at room temperature for 2 h. Ice-water was added and the mixture was stirred for 10 min. The mixture was extracted with CH2Cl2. The organic phase was dried, filtered and concentrated. The residue was purified by chromatography (SiO2, hexane/EtOAc 2:1). Ethyl (RS)-(4-cyano-phenylamino)-(4-hydroxy-3-methylsulphanyl-phenyl)-acetate was obtained as a colorless oil (198 mg, 64%); MS: 343 ([M+H]+).

Aufarbeitung

  1. stirringthe mixture was stirred for 10 min
  2. extractionThe mixture was extracted with CH2Cl2
  3. customThe organic phase was dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography (SiO2, hexane/EtOAc 2:1)

Quellen und Nachweise

ORD-Eintrag
ord-de28f074e9bc4736a189875096fe9715
Quelldatensatz
uspto-grants-2002_11
Patentnummer
US06476264B2

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