Diethyl Ether → 4-Fluorobenzoic Acid

HRID 13735

Reaktionsgleichung

Reaktionsgleichung von HRID 13735
Br([O-])(=O)=O.[Na+].[F:6][C:7]1[CH:14]=[CH:13][C:10]([CH2:11][OH:12])=[CH:9][CH:8]=1.CC[O:17]CC>C(#N)C.O>[F:6][C:7]1[CH:14]=[CH:13][C:10]([C:11]([OH:17])=[O:12])=[CH:9][CH:8]=1

Komponenten

5

Edukt 3

HCID 3283Diethyl EtherHCID 680224-Fluorobenzylic alcoholHCID 23668195Sodium Bromate

Produkt 1

HCID 99734-Fluorobenzoic AcidAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 18373917Acetonitrile--water (1/1)Lösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of the Ceiv catalyst from Example 47 (0.08 g), sodium bromate (0.3 g) and 4-fluorobenzyl alcohol (0.256 g, 2 mmol) in acetonitrile:water (1:1, 10 ml) was stirred at 80° C. for 40 h under an atmosphere of nitrogen. On cooling ether (70 ml) was added and the catalyst was filtered off. The organic layer was separated and the aqueous phase was extracted with ether (2×50 ml). The combined organic extracts were washed with water (25 ml), dried with anhydrous magnesium sulphate and concentrated to give 4-fluorobenzoic acid as a white solid (0.24 g, 86%). M.p. 182° C., lit. 185° C.

Aufarbeitung

  1. additionwas added
  2. filtrationthe catalyst was filtered off
  3. customThe organic layer was separated
  4. extractionthe aqueous phase was extracted with ether (2×50 ml)
  5. washThe combined organic extracts were washed with water (25 ml)
  6. dry with materialdried with anhydrous magnesium sulphate
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-07562343ab814930ba62f565d02c2dcd
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728159B2

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