1,2-Dibromoethane → HCID 59627678, compound

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (0.326 g, 8.14 mmol) was added in one portion to methyl 2-(3,5-difluoro-4-methoxyphenyl)acetate (1.76 g, 8.14 mmol) in DMF (46.3 mL) at 0° C. under nitrogen. The resulting suspension was stirred at 0° C. for 10 minutes. Following this 1,2-dibromoethane (0.772 mL, 8.96 mmol) was added to the reaction mixture and the solution was stirred for 5 minutes. Additional sodium hydride (0.326 g, 8.14 mmol) was then added and the reaction allowed to stir for 2 hours. The reaction mixture was quenched with saturated NH4Cl (50 mL). The reaction mixture was diluted with EtOAc (75 mL), and washed sequentially with water (4×50 mL) and saturated brine (50 mL). The organic layer was evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution at 10% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford methyl 1-(3,5-difluoro-4-methoxyphenyl)cyclopropanecarboxylate (1.540 g, 78%) as a colourless gum.

Provenance & Evidence