Reaction #438529

Reaction equation

1-Bromo-4-fluorobutane

2-fluoro-4-hydroxybenzoic acid

ethanol

potassium hydroxide

→

title compound

Yield 39.1%

2-fluoro-4-(4-fluorobutoxy)benzoic acid

Yield 39.1%

Solvents

water

Conditions

Workup

1. 1
   OtherThe solvent was evaporated under reduced pressure
2. 2
   workup.DISSOLUTIONThe residue was dissolved in water
3. 3
   workup.ADDITIONby adding 1N hydrochloric acid
4. 4
   FiltrationThe insoluble materials were filtered off
5. 5
   Otherdried

Procedure

1-Bromo-4-fluorobutane (3.57 g, 23.1 mmol) was added dropwise to a mixture of 2-fluoro-4-hydroxybenzoic acid (3.00 g, 19.2 mmol), ethanol (11.5 ml) and water (2.3 ml), potassium hydroxide (2.37 g, 42.3 mmol) at 80° C., and the mixture was stirred at 80° C. for 17 hrs. The solvent was evaporated under reduced pressure. The residue was dissolved in water and the solution was acidified by adding 1N hydrochloric acid. The insoluble materials were filtered off and dried to give the title compound (1.73 g) as a pale-brown powder.

Source