Reaktion #159771

Reaktionsgleichung

4-bromo-2-nitro-fluorophenol

15-crown-5

ethyl-1-hydroxycyclopropane carboxylate

sodium hydride

→

1-(4-bromo-2-nitro-phenoxy)-cyclopropanecarboxylic acid ethyl ester

Ausbeute 51.9%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwere added
2. 2
   Sonstigethen quenched by the addition of methanol (1.5 mL)
3. 3
   workup.ADDITIONdiluted with ethyl acetate
4. 4
   WaschenThe mixture was washed with brine
5. 5
   Trocknenthe organic layer was dried over anhydrous sodium sulfate
6. 6
   Einengenconcentrated
7. 7
   Sonstigepurified by silica gel column chromatography

Vorschrift

To a stirred solution of ethyl-1-hydroxycyclopropane carboxylate (2.93 g, 20.5 mmol) in THF (50 mL) was added sodium hydride (60% in mineral oil, 981 mg, 24.5 mmol) under argon atmosphere. After 10 min, 15-crown-5 (0.2 mL) followed by 4-bromo-2-nitro-fluorophenol (4.5 g, 20.5 mmol) were added. The reaction mixture was stirred at room temperature overnight then quenched by the addition of methanol (1.5 mL) and diluted with ethyl acetate. The mixture was washed with brine, and the organic layer was dried over anhydrous sodium sulfate, concentrated and purified by silica gel column chromatography to give 1-(4-bromo-2-nitro-phenoxy)-cyclopropanecarboxylic acid ethyl ester (3.51 g).

Quelle