1-Fluoro-3-iodobenzene

Chemical Properties

Uses

General Description

Synthesis

372-19-0

1121-86-4

The general procedure for the synthesis of m-fluoroiodobenzene from 3-fluoroaniline was as follows: an aqueous solution (20 mL) of NaNO2 (6.4 g, 92.75 mmol) was slowly added dropwise at 0 °C to a solution of 3-fluoroaniline (10 g, 90.09 mmol) dissolved in 32% H2SO4 (179 g). The reaction mixture was stirred continuously at 0 °C for 1 hour. Subsequently, an aqueous solution (30 mL) of KI (22.4 g, 134.94 mmol) was added while maintaining 0 °C and stirring was continued at 0 °C for 1 hour. After completion of the reaction, the aqueous phase was extracted with EtOAc (2 x 250 mL). The organic phases were combined and washed sequentially with water (5×200mL) and 10% NaHSO3 solution (3×200mL), dried over Na2SO4 and concentrated under reduced pressure to remove the solvent, yielding 17.7 g of 1-fluoro-3-iodobenzene as a yellow solid in 82% yield.

References