1,6-Dibromohexane → 1-(4-((6-Bromohexyl)oxy)butyl)-4-nitrobenzene

HRID 385261

Reaktionsgleichung

Reaktionsgleichung von HRID 385261
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][CH2:13][OH:14])=[CH:6][CH:5]=1)([O-:3])=[O:2].[Br:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]Br.[OH-].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[Br:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][O:14][CH2:13][CH2:12][CH2:11][CH2:10][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=1

Komponenten

6

Edukt 3

HCID 123681,6-DibromohexaneHCID 14798Sodium HydroxideHCID 5908694-Nitrobenzenebutanol

Produkt 1

HCID 200714241-(4-((6-Bromohexyl)oxy)butyl)-4-nitrobenzeneAusbeute 20,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 94433Tetrabutylammonium hydrogen sulfateKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A stirred mixture of 4-(4-nitrophenyl)butan-1-ol (2.0 g, 10 mmol), tetra-n-butylammonium hydrogen sulfate (0.17 g, 0.5 mmol), and 1,6-dibromohexane (3.2 mL, 20 mmol) in dichloromethane (10 mL) was treated with aqueous sodium hydroxide solution (10 M, 1 mL). The reaction mixture was stirred for 6 days at room temperature. The organic and aqueous phases were separated. The aqueous phase was extracted thrice with dichloromethane. The combined organics were washed with water, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified via automated flash silica gel chromatography, using a 40 g SiliSep flash column (hexanes/ethyl acetate). Concentration of the desired fractions under reduced pressure provided the title compound as a pale straw-colored oil (0.72 g, 20%). ES/MS calcd. for C16H25BrNO3+ 358.1. found m/z=358.2 (M+H)+.

Aufarbeitung

  1. customThe organic and aqueous phases were separated
  2. extractionThe aqueous phase was extracted thrice with dichloromethane
  3. washThe combined organics were washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude residue was purified via automated flash silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-4c8c44fec77d4d0d95a1d54e83851b3a
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367829B2

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