Sodium hydride → 1-(4-Bromo-2-nitro-phenoxy)-cyclopropanecarboxylic acid ethyl ester

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).

1. additionwere added
2. customthen quenched by the addition of methanol (1.5 mL)
3. additiondiluted with ethyl acetate
4. washThe mixture was washed with brine
5. dry with materialthe organic layer was dried over anhydrous sodium sulfate
6. concentrationconcentrated
7. custompurified by silica gel column chromatography

ORD-Eintrag

ord-b015f7ca02f54c3cb9caa1ce1e96bd8e

Quelldatensatz

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08828951B2