Acetyl chloride → Methyl 3-bromo-5-hydroxybenzoate

HRID 1051064Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1051064
[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:12](Cl)(C)=O>CO.CC(=O)OCC>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([OH:11])[CH:10]=1)[C:5]([O:7][CH3:12])=[O:6]

Komponenten

5

Edukt 2

HCID 6367Acetyl chlorideHCID 157355113-Bromo-5-hydroxybenzoic acid

Produkt 1

HCID 53216607Methyl 3-bromo-5-hydroxybenzoateAusbeute 98,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a flask containing 3-bromo-5-hydroxybenzoic acid (2.0 g, 9.2 mmol) in anhydrous MeOH (10 mL) at 0° C. under N2 was added AcCl (912 μL, 12.9 mmol). The reaction mixture was allowed to warm to room temperature overnight. The mixture was diluted with EA and washed with NaHCO3. The organic layers were dried and concentrated to provide 2.1 g (97%) of methyl 3-bromo-5-hydroxybenzoate as a white solid. LCMS-ESI (m/z) calculated for C8H7BrO3: 231.04. found 232.9 [M+H]+, tR=3.06 min.

Aufarbeitung

  1. washwashed with NaHCO3
  2. customThe organic layers were dried
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-6e455b4139de435d90538567cb120cc0
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09388147B2

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