Tetrahydrofuran → 2-Fluoromethyl-2-amino-3-pentenenitrile

Temperature

-40 °C

Under an atmosphere of nitrogen, propenyl magnesium bromide is prepared from magnesium turnings (9.8 g, 400 mmol), freshly distilled 1-bromo-1-propene (24.2 g, 200 mmol) and 200 ml of dry tetrahydrofuran. After removing the Grignard solution from the excess of magnesium and cooling to -40° C., fluoroacetonitrile (11.8 g, 200 mmol) in tetrahydrofuran (70 ml) is added during 15 min. The reaction mixture is then poured into a solution of sodium cyanide (40 g) and ammonium chloride (59 g) in water (400 ml) and kept 1 hour at room temperature. After saturation with sodium chloride, the tetrahydrofuran layer is separated and evaporated under reduced pressure. The residue is dissolved in diethyl ether, washed with water, dried with sodium sulfate and evaporated to give crude 2-fluoromethyl-2-amino-3-pentenenitrile (1:1 cis/trans mixture, 21.5 g) as a dark coloured oil which is used for the next step without further purification.

1. customAfter removing the Grignard solution from the excess of magnesium
2. customAfter saturation with sodium chloride, the tetrahydrofuran layer is separated
3. customevaporated under reduced pressure
4. dissolutionThe residue is dissolved in diethyl ether
5. washwashed with water
6. dry with materialdried with sodium sulfate
7. customevaporated

ORD record

ord-dc8e288b95fc4fe5b3c377e9bc130394

Source dataset

uspto-grants-1983_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04405530