Acetonitrile → 3-Amino-3-(4-fluorophenyl)acrylonitrile

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Reaction Steps

The procedure of Example 1 was used to react 2.7 grams (0.117 mole) of sodium and 5.2 grams (0.126 mole) of acetonitrile with 10.0 grams (0.083 mole) of p-fluorobenzonitrile. After the addition of water, the reaction mixture was extracted three times with chloroform. The combined chloroform extracts were concentrated to obtain a dark-colored crystalline mass which was recrystallized four times from a mixture of chloroform and hexane to obtain yellow plates of β-amino-β-(p-fluorophenyl)acrylonitrile, mleting point 110°-112°C. Analysis: -- Calculated for C9H7N2F (percent): C, 66.66; H, 4.35; N, 17.27; F, 11.72. Found (percent): C, 66.48; H, 4.34; N, 17.21; F, 11.19.

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