Reaction #42013

Reaction equation

sodium bromate

4-fluorobenzyl alcohol

ether

→

4-fluorobenzoic acid

Yield 86.0%

Solvents

acetonitrile water

Conditions

Workup

1. 1
   workup.ADDITIONwas added
2. 2
   Filtrationthe catalyst was filtered off
3. 3
   OtherThe organic layer was separated
4. 4
   Extractionthe aqueous phase was extracted with ether (2×50 ml)
5. 5
   WashThe combined organic extracts were washed with water (25 ml)
6. 6
   Dryingdried with anhydrous magnesium sulphate
7. 7
   Concentrationconcentrated

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.

Source