2-Fluorophenylacetic acid

Chemical Properties

white to off-white shiny crystals or crystalline

Uses

2-Fluorophenylacetic acid was used:

• in the synthesis of thiazolino[3,2-c]pyrimidin-5,7-diones and N-[2-(3,4-dichlorophenyl)-ethyl]-N′-[2-(2-fluorophenyl)-ethyl]-ethane-1,2-diamine
• as chiral derivatizing agent for determination of enantiomeric composition of chiral, nonracemic compounds by ¹⁹F NMR spectroscopy

General Description

2-Fluorophenylacetic acid is chiral derivatizing agent for determination of enantiomeric composition of chiral, nonracemic compounds by ¹⁹F NMR spectroscopy.

Synthesis

The Schlenk tube was heated under a high vacuum, pre-dried with calcium chloride, and filled with CO2 gas. Bis(4-methoxyphenyl)zinc magnesium chloride lithium chloride (12.8 ml, 0:39 M in THF, 5.0 mmol) was added, and CO2 was passed through the solution for 5 minutes. The reaction mixture was stirred at 25 °C for 6 hours. Diethyl ether (50 ml) was added, and the organic phase was extracted with 2M NaOH (3×50 ml). The combined aqueous phases were acidified with 2M HCl (pH <5) and extracted with diethyl ether (3×50 ml). The combined organic phases were dried over sodium sulfate, and the solvent was removed in vacuo. 2-Fluorophenylacetic acid was obtained in a yield of 100%.