Water → Methyl 4-[(5-bromopentyl)thio]benzoate

HRID 68645Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 68645
[SH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[Br:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]Br.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Br:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][S:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 81001,5-DibromopentaneHCID 11430Potassium CarbonateHCID 237573Methyl 4-sulfanylbenzoate

Produkt 1

HCID 67164237Methyl 4-[(5-bromopentyl)thio]benzoateAusbeute 73,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of methyl 4-mercaptobenzoate (3.39 g) and 1,5-dibromopentane (9.31 g) in dimethyl formamide (100 mL), potassium carbonate (3.07 g) was added. The reaction mixture was stirred at room temperature for 3 hours. To the reaction mixture, water (300 mL) was added and the aqueous layer was extracted twice with an n-hexane-ethyl acetate solution (n-hexane:ethyl acetate=1:1) (150 mL). The combined organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and then concentrated. The residue was purified by silica gel chromatography (n-hexane:ethyl acetate=1:0→8:2) to obtain the title compound (4.69 g) having the following physical properties.

Aufarbeitung

  1. extractionthe aqueous layer was extracted twice with an n-hexane-ethyl acetate solution (n-hexane:ethyl acetate=1:1) (150 mL)
  2. washThe combined organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography (n-hexane:ethyl acetate=1:0→8:2)

Quellen und Nachweise

ORD-Eintrag
ord-7d5896dd4e01455cb6d9d5d82932a3be
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822459B2

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