Pyridine → 2-Pivaloyloxy-5-bromo-6-methylbenzoic acid

HRID 365960

Reaktionsgleichung

Reaktionsgleichung von HRID 365960
[OH:1][C:2]1[CH:10]=[CH:9][C:8]([Br:11])=[C:7]([CH3:12])[C:3]=1[C:4]([OH:6])=[O:5].[C:13](Cl)(=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15].O1CCCC1.N1C=CC=CC=1>O.C(OCC)(=O)C>[C:13]([O:1][C:2]1[CH:10]=[CH:9][C:8]([Br:11])=[C:7]([CH3:12])[C:3]=1[C:4]([OH:6])=[O:5])(=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15]

Komponenten

7

Edukt 4

HCID 1049PyridineHCID 8028TetrahydrofuranHCID 62493Pivaloyl chlorideHCID 110534513-Bromo-6-hydroxy-2-methylbenzoic acid

Produkt 1

HCID 232932342-Pivaloyloxy-5-bromo-6-methylbenzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 1B (6.45 g, 28 mmol), pivaloylchloride (3.62 g, 30 mmol), tetrahydrofuran (60 ml) and pyridine (2.45 ml) is stirred at room temperature for 16 hours. The reaction mixture is diluted with water and ethyl acetate. The organic phase is washed with water twice. The organic phase is concentrated in vacuo and the residue is re-crystallized from petrol ethers/diisopropylether (9:1 v/v) yielding the pure product as a white crystals, 6.3 g, (71.6%), mp. 144-145° C.

Aufarbeitung

  1. washThe organic phase is washed with water twice
  2. concentrationThe organic phase is concentrated in vacuo
  3. customthe residue is re-crystallized from petrol ethers/diisopropylether (9:1 v/v)

Quellen und Nachweise

ORD-Eintrag
ord-32e49ff7cf8e465b838d4cd342ec1d7d
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06127570

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