3-(2-bromo-4,5-dimethoxyphenyl)propanenitrile

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of NaNH2, prepared starting from 200 mL of liquid NH3 and 1 g of Na (catalyst: FeCl3) there are added, in portions, 5.4 g of 3-(2-bromo-4,5-dimethoxyphenyl)propanenitrile and the reaction mixture is stirred at ambient temperature for 2 hours. After evaporating off the excess NH3, 2 g of NH4Cl and 200 mL of water are added in portions. The grey crystals formed are collected and recrystallised from ethanol to yield 2.38 g of the expected product. After evaporating off the excess NH3, 2 g of NH4Cl and 200 mL of water are added in portions The grey crystals formed are collected recrystallised from ethanol

Conditions: temp:-60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 0.3 mL of acetonitrile (5.8 mmoles, 1.8 eq.) in 15 mL of THF there are added, at −60° C., 1.77 mL of n-butyllithium (2M in cyclohexane, 3.5 mmoles, 1.1 eq.). The solution is stirred for 15 minutes at −60° C. and then 1 g of 1-bromo-2-(bromomethyl)-4,5-dimethoxybenzene (3.2 mmoles) dissolved in 5 mL of THF is added. The reaction mixture is stirred for 1 hour and then hydrolysed using 10 mL of water and extracted twice with ethyl acetate. The organic phases are combined and evaporated under reduced pressure. The crude reaction product is purified by chromatography on silica gel (eluant: methylcyclohexane/ethyl acetate (70/30)). After evaporating off the solvent under reduced pressure, 505 mg of an orange oil which crystallises in the form of a beige solid are obtained. is added The reaction mixture is stirred for 1 hour extracted twice with ethyl acetate evaporated under reduced pressure The crude reaction product is purified by chromatography on silica gel (eluant: methylcyclohexane/ethyl acetate (70/30)) After evaporating off the solvent under reduced pressure, 505 mg of an orange oil which crystallises in the form of a beige solid are obtained

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of NaNH2, prepared starting from 200 mL of liquid NH3 and 1 g of Na (catalyst: FeCl3) there are added, in portions, 5.4 g of 3-(2-bromo-4,5-dimethoxyphenyl)propanenitrile and the reaction mixture is stirred at ambient temperature for 2 hours. After evaporating off the excess NH3, 2 g of NH4Cl and 200 mL of water are added in portions. The grey crystals formed are collected and recrystallised from ethanol to yield 2.38 g of the expected product. After evaporating off the excess NH3, 2 g of NH4Cl and 200 mL of water are added in portions The grey crystals formed are collected recrystallised from ethanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of 21 g of 3-(3,4-dimethoxyphenyl)propanenitrile, 10.3 g of sodium acetate and 400 mL of acetic acid there are added 20 g of dibromine in 50 mL of acetic acid. The resulting reaction mixture is stirred overnight and then poured into water and extracted with benzene. The organic phase is washed with aqueous sodium thiosulphate solution and then with water, dried over sodium sulphate and concentrated under reduced pressure. The crude reaction product is purified on a silica column (eluant: benzene), and the product obtained is recrystallised from ethanol to yield 19.3 g of the expected product. The resulting reaction mixture extracted with benzene The organic phase is washed with aqueous sodium thiosulphate solution with water, dried over sodium sulphate concentrated under reduced pressure The crude reaction product is purified on a silica column (eluant: benzene) the product obtained is recrystallised from ethanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of NaNH2, prepared starting from 200 mL of liquid NH3 and 1 g of Na (catalyst: FeCl3) there are added, in portions, 5.4 g of 3-(2-bromo-4,5-dimethoxyphenyl)propanenitrile and the reaction mixture is stirred at ambient temperature for 2 hours. After evaporating off the excess NH3, 2 g of NH4Cl and 200 mL of water are added in portions. The grey crystals formed are collected and recrystallised from ethanol to yield 2.38 g of the expected product. After evaporating off the excess NH3, 2 g of NH4Cl and 200 mL of water are added in portions The grey crystals formed are collected recrystallised from ethanol

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 1 g (5.3 mmoles) of 3-(3,4-dimethoxyphenyl)propanenitrile in 42 mL of DMF is cooled to 0° C. To the resulting solution there is added, little by little, 0.93 g of NBS (5.2 mmoles, 1 eq.). After stirring for 30 minutes at 0° C., the reaction mixture is brought back to ambient temperature and stirred for two hours. It is then hydrolysed using 170 mL of water and extracted twice with 130 mL of ethyl acetate. The organic phases are collected and then washed, first with saturated aqueous Na2S2O5 solution and then with water. After evaporating off the solvent under reduced pressure, 1.29 g of a colourless oil which crystallises into a white solid are obtained. To the resulting solution there is added is brought back to ambient temperature stirred for two hours extracted twice with 130 mL of ethyl acetate The organic phases are collected washed, first with saturated aqueous Na2S2O5 solution After evaporating off the solvent under reduced pressure, 1.29 g of a colourless oil which crystallises into a white solid are obtained