Ethyl bromoacetate → 3-Amino-3-cyclopropyl-acrylic acid ethyl ester

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Reaction Steps

Cyclopropanecarbonitrile (2.7 g, 40.5 mmol) was dissolved in dry THF (100 mL) and firstly zinc (13.2 g, 202.3 mmol) and then zinc oxide (1.6 g, 20.2 mmol) were added followed by dropwise addition of ethylbromoacetate (6.7 g, 40.5 mmol). The mixture was sonicated in a 35 kHz ultrasonic bath under N2 for 2 hours. After 30 minutes a green colour was observed. The mixture was filtered through celite to remove the zinc and zinc oxide. The filtrate was added to 20 ml of 50% K2CO3 (aq) solution. A thick precipitate formed which was filtered to remove the solid and the aqueous was extracted with 100 ml EtOAc. The extract was washed with 20 ml brine, dried over MgSO4 and concentrated in vacuo to give the crude product (3.8 g). The crude material was purified by column chromatography on silica gel eluting with 90:10 pentane:EtOAc to give the title compound (1.32 g) as a yellow oil.

Provenance & Evidence