StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

1,4-Dibromobenzene → (R)-N-((R)-(4-bromophenyl)(2,4-difluorophenyl)methyl)-2-methylpropane-2-sulfinamide

HRID 1525263
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1525263
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][CH:3]=1.[Li]CCCC.[F:14][C:15]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:16]=1/[CH:17]=[N:18]/[S@@:19]([C:21]([CH3:24])([CH3:23])[CH3:22])=[O:20]>C1COCC1>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([C@H:17]([C:16]2[CH:25]=[CH:26][C:27]([F:29])=[CH:28][C:15]=2[F:14])[NH:18][S@@:19]([C:21]([CH3:24])([CH3:23])[CH3:22])=[O:20])=[CH:3][CH:4]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 78041,4-DibromobenzeneHCID 88931146(NE,R)-N-[(2,4-difluorophenyl)methylidene]-2-methylpropane-2-sulfinamide2×HCID 178418339Butyllithium

Produkt 1

HCID 89462573(R)-N-((R)-(4-bromophenyl)(2,4-difluorophenyl)methyl)-2-methylpropane-2-sulfinamideAusbeute 22 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel
2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

1,4-dibromobenzene (9.6 g, 40.77 mmol) was dissolved in THF (150 ml) and cooled to −78° C. under nitrogen. Then n-BuLi (16.3 ml, 40.77 mmol) was added dropwise below −60° C. After addition, the mixture was stirred at −78° C. for additional 1 h and then (R,E)-N-(2,4-difluorobenzylidene)-2-methylpropane-2-sulfinamide, 20-b, (10 g, 40.77 mmol) in anhydrous THF was added dropwise below −60° C. Then the mixture was allowed to stir at room temperature for 6 h. The mixture was quenched with saturated NH4Cl followed by extraction with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under vacuum. The residue was purified by column chromatography (petroleum ether/ethyl acetate=4/1) to provide the product, 20-c, (3.6 g, 22%). HPLC indicated that the no obvious diastereomer was observed.

Aufarbeitung

  1. additionAfter addition
  2. stirringto stir at room temperature for 6 h
  3. customThe mixture was quenched with saturated NH4Cl
  4. extractionfollowed by extraction with ethyl acetate
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by column chromatography (petroleum ether/ethyl acetate=4/1)

Quellen und Nachweise

ORD-Eintrag
ord-cc59571dc43b4ee58d9a2529bab6f998
Quelldatensatz
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09079930B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion