Water → HCID 57435890, Verbindung

HRID 30581Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 30581
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]O)[CH:5]=[CH:6][CH:7]=1.C(N(S(F)(F)[F:20])CC)C.O>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][F:20])[CH:3]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 123472(Diethylamino)sulfur trifluorideHCID 57435887931430-20-5

Produkt 1

HCID 57435890HCID 57435890, VerbindungAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of 5-(3-bromophenyl)pentan-1-ol (0.63 g, 2.6 mmol) in methylene chloride at −78° C. was treated with a solution of diethylamino sulfur trifluoride (DAST) (0.7 mL, 5.2 mmol) in methylene chloride, allowed to warm to room temperature, stirred for 0.5 h at room temperature, poured into water and extracted with ether. The extracts were combined washed sequentially with saturated sodium bicarbonate and water, dried over magnesium sulfate and concentrated under reduced pressure. The concentrate was purified by flash chromatography on silica gel, 40:1 hexane/ethyl acetate as eluent to give 1-bromo-3-(5-fluoropentyl)benzene as a pale yellow oil, 0.4 g (63% yield); 1H NMR (DMSO-d6) δ 1.3 (m, 2H); 1.6 (m, 4H); 2.5 (t, 2 H); 4.4 (dxt, 2H); 7.2 (m, 2 H); 7.4 (m, 2 H); MS [(+)ESI] m/z=245 [M−H]+.

Aufarbeitung

  1. extractionextracted with ether
  2. washThe extracts were combined washed sequentially with saturated sodium bicarbonate and water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe concentrate was purified by flash chromatography on silica gel, 40:1 hexane/ethyl acetate as eluent

Quellen und Nachweise

ORD-Eintrag
ord-edecd3fd90264d50b6719419c29acc58
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423158B2

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