toluene-4-sulfonic acid (S)-2-(3-bromophenyl)-2-fluoro-ethyl ester → 1-bromo-(S)-3-(1-fluoropent-4-en-1-yl)benzene

HRID 30603Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 30603
[Br:1][C:2]1[CH:3]=[C:4]([C@H:8]([F:21])[CH2:9]OS(C2C=CC(C)=CC=2)(=O)=O)[CH:5]=[CH:6][CH:7]=1.[CH2:22]([Mg]Br)[CH:23]=[CH2:24]>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C@@H:8]([F:21])[CH2:9][CH2:24][CH:23]=[CH2:22])[CH:3]=1

Komponenten

4

Edukt 2

HCID 59790335toluene-4-sulfonic acid (S)-2-(3-bromophenyl)-2-fluoro-ethyl esterHCID 178455850HCID 178455850, Verbindung

Produkt 1

HCID 686490871-bromo-(S)-3-(1-fluoropent-4-en-1-yl)benzene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of toluene-4-sulfonic acid (S)-2-(3-bromophenyl)-2-fluoro-ethyl ester (5 mmol) in THF at room temperature is treated dropwise with a 1M solution of allylmagnesium bromide, stirred at room temperature for 5 h, quenched with saturated NH4Cl and extracted with ethyl acetate. The extracts are combined, washed sequentially with water and brine, dried over MgSO4 and concentrated in vacuo to afford 1-bromo-(S)-3-(1-fluoropent-4-en-1-yl)benzene.

Aufarbeitung

  1. customquenched with saturated NH4Cl
  2. extractionextracted with ethyl acetate
  3. washwashed sequentially with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e5904cd7f23f453db929e9aa454f32c8
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423158B2

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