Tetrahydrofuran → 2-Fluoro-4-chloro-5cyclopentyloxyphenylhydrazine

Participants

Reaction Steps

To a solution of tin (II) chloride monohydrate (200 g, 0.886 mol) dissolved in concentrated hydrochloric acid (200 ml) and THF (200 ml) was added a THF (200 ml) solution of 2-fluoro-4-chloro-5-cyclopentyloxyphenyl-diazonium fluoroborate (31.3 g, 0.094 mol) under cooling at 0° to 5° C. After stirring for 8 hours at that temperature, an aqueous solution (1,000 ml) of potassium hydroxide (160 g) was added thereto. The solid that was formed was separated by filtration, and the filtrate was extracted with ethyl acetate (1,000 ml×3). The extract was washed with a saturated aqueous solution of sodium chloride (1,000 ml), and dried over anhydrous magnesium sulfate. The drying agent was separated by lilt:ration, and the solvent was distilled off under reduced pressure to obtain 2-fluoro-4-chloro-5-cyclopentyloxyphenylhydrazine as brown crystals (20.9 g, 85.64 yield).

Provenance & Evidence