Methanol → Methyl 4-bromo-alpha-hydroxybenzeneacetate

HRID 547092

Reaktionsgleichung

Reaktionsgleichung von HRID 547092
C[Si](C=[N+]=[N-])(C)C.[CH3:8]CCCCC.[Br:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]([OH:25])[C:22]([OH:24])=[O:23])=[CH:17][CH:16]=1.CO>C1C=CC=CC=1>[CH3:8][O:23][C:22](=[O:24])[CH:21]([C:18]1[CH:17]=[CH:16][C:15]([Br:14])=[CH:20][CH:19]=1)[OH:25]

Komponenten

6

Edukt 4

HCID 887MethanolHCID 8058HexaneHCID 97930p-Bromomandelic acidHCID 167693Trimethylsilyldiazomethane

Produkt 1

HCID 14571696Methyl 4-bromo-alpha-hydroxybenzeneacetateAusbeute 93,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

A solution of trimethylsilyldiazomethane in hexane (2 M, 1.4 mL, 2.8 mmol) was added to a solution of 4-bromo-phenyl-hydroxy-acetic acid (506 mg, 2.19 mmol) in benzene (2.1 mL)-methanol (1.0 mL) under cooling with ice, and the mixture was stirred at room temperature for five minutes. The reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate=3/1) to give the title compound (500 mg, 93%).

Aufarbeitung

  1. temperatureunder cooling with ice
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate=3/1)

Quellen und Nachweise

ORD-Eintrag
ord-b20975e893d9451080f5f154d764a445
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07935688B2

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