2,5-Dimethylbenzoic acid → 3-Bromo-2,5-dimethylbenzoic acid

HRID 1187063Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1187063
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[Br:12]N1C(=O)CCC1=O>S(=O)(=O)(O)O>[Br:12][C:10]1[C:2]([CH3:1])=[C:3]([CH:7]=[C:8]([CH3:11])[CH:9]=1)[C:4]([OH:6])=[O:5]

Komponenten

4

Edukt 2

HCID 118922,5-Dimethylbenzoic acidHCID 67184N-bromobutanimide

Produkt 1

HCID 592382453-Bromo-2,5-dimethylbenzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 2,5-dimethylbenzoic acid (20 g, 133 mmol) in 100 mL of conc. sulfuric acid was cooled to 0° C., and then N-bromosuccinimide (24 g, 139 mmol) was added. The reaction was stirred at 0° C. for 1.5 hours. The mixture was poured onto ice/water, extracted with EtOAc, washed with brine, dried over anhydrous sodium sulfate and concentrated. The crude product was purified by column chromatography to afford 3-bromo-2,5-dimethylbenzoic acid.

Aufarbeitung

  1. additionThe mixture was poured onto ice/water
  2. extractionextracted with EtOAc
  3. washwashed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-ca509dcd35124490af3820ae57bd76e8
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08673920B2

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