Diethyl Ether → 4-Fluorobenzoic Acid

HRID 13735

Reaction equation

HRID 13735 reaction equation
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

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 680224-Fluorobenzylic alcoholHCID 23668195Sodium Bromate

Product 1

HCID 99734-Fluorobenzoic AcidYield 86%

Reagents, catalysts & solvents 1

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

Conditions

Temperature
80 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-07562343ab814930ba62f565d02c2dcd
Source dataset
uspto-grants-2010_06
Patent number
US07728159B2

Linked notes

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