Benzyl Bromide → Benzyl 3-bromo-5-hydroxybenzoate

HRID 332657Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 332657
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([OH:11])[CH:10]=1)[C:5]([OH:7])=[O:6].C(=O)([O-])[O-].[K+].[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C)C=O.O>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([OH:11])[CH:10]=1)[C:5]([O:7][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:6]

Komponenten

6

Edukt 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 157355113-Bromo-5-hydroxybenzoic acid

Produkt 1

HCID 71093147Benzyl 3-bromo-5-hydroxybenzoateAusbeute 100,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a stirred solution of 3-bromo-5-hydroxybenzoic acid (2 g, 9.22 mmol) in dimethyl formamide (50 mL), was added potassium carbonate (1.27 g, 9.21 mmol), and the mixture was stirred at 0° C. for 20 minutes. Benzyl bromide (1.1 mL, 9.25 mmol) was added, and the reaction mixture allowed to warm to room temperature over 16 hours. The reaction mixture was diluted with water and extracted with ethyl acetate (×3). The combined organic extracts were washed with brine, dried (magnesium sulphate), filtered, and concentrated under reduced pressure to afford the title compound (2.85 g, quantitative yield).

Aufarbeitung

  1. temperatureto warm to room temperature over 16 hours
  2. extractionextracted with ethyl acetate (×3)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (magnesium sulphate)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b84a3e732df34143b7f55f33667b13c4
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877774B2

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