Réaction #49769

Équation de réaction

tin (II) chloride monohydrate

potassium hydroxide

THF

THF

2-fluoro-4-chloro-5-cyclopentyloxyphenyl-diazonium fluoroborate

→

2-fluoro-4-chloro-5-cyclopentyloxyphenylhydrazine

Solvants

hydrochloric acid

Conditions de réaction

Traitement

1. 1
   Températureunder cooling at 0° to 5° C
2. 2
   AutreThe solid that was formed
3. 3
   Autrewas separated by filtration
4. 4
   Extractionthe filtrate was extracted with ethyl acetate (1,000 ml×3)
5. 5
   LavageThe extract was washed with a saturated aqueous solution of sodium chloride (1,000 ml)
6. 6
   Séchagedried over anhydrous magnesium sulfate
7. 7
   AutreThe drying agent was separated by lilt:ration
8. 8
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
9. 9
   Autreto obtain

Mode opératoire

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).

Source