Hexane → (Z)-tert-butyl (1-(5-bromo-2-fluorophenyl)-2,2-difluoroethylidene)carbamate

HRID 2196309Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2196309
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:13])=[C:6]([C:8](=O)[CH:9]([F:11])[F:10])[CH:7]=1.[CH3:14][C:15]([O:18][C:19](=[O:40])[N:20]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([CH3:17])[CH3:16].CCCCCC.C1(P(=O)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1>[C:15]([O:18][C:19](=[O:40])/[N:20]=[C:8](/[C:6]1[CH:7]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=1[F:13])\[CH:9]([F:11])[F:10])([CH3:17])([CH3:16])[CH3:14]

Komponenten

6

Edukt 4

HCID 8058HexaneHCID 13097Triphenylphosphine OxideHCID 2756802N-Boc-Imino-(triphenyl)phosphoraneHCID 548578331-(5-Bromo-2-fluorophenyl)-2,2-difluoroethanone

Produkt 1

HCID 87096325(Z)-tert-butyl (1-(5-bromo-2-fluorophenyl)-2,2-difluoroethylidene)carbamateAusbeute 51,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A suspension of 1-(5-bromo-2-fluoro-phenyl)-2,2-difluoro-ethanone (16.0 g, 63.2 mmol) and N-(triphenylphosphoranylidene)-carbamic acid 1,1-dimethylethyl ester (CAS 68014-21-1) (26.3 g, 69.6 mmol) in 12 ml toluene was stirred at 100° C. for 2 days. The suspension became clear. After being cooled down somewhat, hexane was added till crystallization of triphenylphosphine oxide started. The mixture was filtered and the filtrate was purified by chromatography on silica gel with hexane/TBME 1-5% to give 11.37 g of the title compound as a yellow liquid.

Aufarbeitung

  1. temperatureAfter being cooled down somewhat
  2. filtrationThe mixture was filtered
  3. customthe filtrate was purified by chromatography on silica gel with hexane/TBME 1-5%

Quellen und Nachweise

ORD-Eintrag
ord-5c131a8a8afe4d80a12fc8f74aabd2da
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08338413B1

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