1,6-Dibromohexane → [[4-[(6-Bromohexyl)oxy]butyl]thio]benzene

HRID 2108114

Reaktionsgleichung

Reaktionsgleichung von HRID 2108114
[C:1]1([S:7][CH2:8][CH2:9][CH2:10][CH2:11][OH:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]Br.[OH-].[Na+]>O>[Br:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][O:12][CH2:11][CH2:10][CH2:9][CH2:8][S:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

5

Edukt 3

HCID 123681,6-DibromohexaneHCID 14798Sodium HydroxideHCID 2837984-(Phenylsulfanyl)butan-1-ol

Produkt 1

HCID 54422842[[4-[(6-Bromohexyl)oxy]butyl]thio]benzeneAusbeute 55,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

4-(Phenylthio)-1-butanol (5.25 g), 1,6-dibromohexane (21.08 g), TAB (1 g) and 40% sodium hydroxide solution (45 ml) were stirred together at room temperature for 18 h. The mixture was diluted with water (150 ml), extracted with diethyl ether (2×150 ml), the organic layer washed with brine (100 ml), dried and evaporated in vacuo to give an oil. Purification by FCC eluting with System A (0:20→1:19) gave the title compound (5.54 g) as a colourless oil. T.l.c. (System A 1:9) Rf 0.12.

Aufarbeitung

  1. extractionextracted with diethyl ether (2×150 ml)
  2. washthe organic layer washed with brine (100 ml)
  3. customdried
  4. customevaporated in vacuo
  5. customto give an oil
  6. customPurification by FCC
  7. washeluting with System A (0:20→1:19)

Quellen und Nachweise

ORD-Eintrag
ord-036ed0531d0c4a5999ddfd116adebb00
Quelldatensatz
uspto-grants-1990_06
Patentnummer
US04937268

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