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

HRID 1525269
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Reaktionsgleichung

Reaktionsgleichung von HRID 1525269
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
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Komponenten

5

Edukt 3

HCID 78041,4-DibromobenzeneHCID 89462916(NE,S)-N-[(2,4-difluorophenyl)methylidene]-2-methylpropane-2-sulfinamide2×HCID 178418339Butyllithium

Produkt 1

HCID 89462687(S)-N-((S)-(4-bromophenyl)(2,4-difluorophenyl)methyl)-2-methylpropane-2-sulfinamideAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel
2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

1,4-dibromobenzene (10.58 g, 44.8 mmol) was dissolved in THF (150 ml) and cooled to −78° C. under nitrogen. Then n-BuLi (18 ml, 44.8 mmol) was added dropwise below −60° C. After addition, the mixture was stirred at −78° C. for additional 1 h and then (S,E)-N-(2,4-difluorobenzylidene)-2-methylpropane-2-sulfinamide, 21-a, (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, 21-b, (7.5 g, 42%). HPLC implicated that only the single isomer was formed.

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-30d27f901b554df69c00ea7cec738ae1
Quelldatensatz
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09079930B2

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