2-(4-fluoro-2,6-dimethylphenyl)acetonitrile

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:200.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1.30 g (8 mmol) (4-fluoro-2,6-dimethyl-phenyl)-acetonitrile, 3.83 g (4.27 ml, 64 mmol) ethylene diamine and 0.128 g (4 mmol) sulfur in a pressurized glass tube was heated under microwave irradiation to 200° C. for 20 min. The cooled reaction mixture was poured onto water, extracted with methylene chloride, the combined extracts washed with brine, dried over Na2SO4, filtered and evaporated. Purification of the residue by flash-chromatography over silica gel with a ethyl acetate/methanol gradient containing 1% conc. ammonia provided 2-(4-fluoro-2,6-dimethyl-benzyl)-4,5-dihydro-1H-imidazole as light yellow solid: MS (EI): 206.1 ((M+.), 100%). The cooled reaction mixture was poured onto water extracted with methylene chloride the combined extracts washed with brine dried over Na2SO4 filtered evaporated Purification of the residue by flash-chromatography over silica gel with a ethyl acetate/methanol gradient containing 1% conc. ammonia

Conditions: temp:200.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1.30 g (8 mmol) (4-fluoro-2,6-dimethyl-phenyl)-acetonitrile, 3.83 g (4.27 ml, 64 mmol) ethylene diamine and 0.128 g (4 mmol) sulfur in a pressurized glass tube was heated under microwave irradiation to 200° C. for 20 min. The cooled reaction mixture was poured onto water, extracted with methylene chloride, the combined extracts washed with brine, dried over Na2SO4, filtered and evaporated. Purification of the residue by flash-chromatography over silica gel with a ethyl acetate/methanol gradient containing 1% conc. ammonia provided 2-(4-fluoro-2,6-dimethyl-benzyl)-4,5-dihydro-1H-imidazole as light yellow solid: MS (EI): 206.1 ((M+.), 100%). The cooled reaction mixture was poured onto water extracted with methylene chloride the combined extracts washed with brine dried over Na2SO4 filtered evaporated Purification of the residue by flash-chromatography over silica gel with a ethyl acetate/methanol gradient containing 1% conc. ammonia

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

Procedure: A solution of 1.86 g (9 mmol) 2,6-dimethyl-4-fluoro-benzyl bromide and 0.420 g (9 mmol) sodium cyanide in 21 ml ethanol/water 6:1 was heated to reflux for 4h. The cooled reaction mixture was concentrated and extracted with ethyl acetate. The combined extracts were washed with brine, dried over Na2SO4, filtered and evaporated. Filtration of the residue through a silica gel pad with heptane/ethyl acetate 1:1 provided (4-fluoro-2,6-dimethyl-phenyl)-acetonitrile as colourless solid: MS (EI): 163.1 (M+.), 148.1 ((M-CH3)+.), 136.1 ((M-HCN)+., 100%). to reflux for 4h The cooled reaction mixture was concentrated extracted with ethyl acetate The combined extracts were washed with brine dried over Na2SO4 filtered evaporated Filtration of the residue through a silica gel pad with heptane/ethyl acetate 1:1 provided (4-fluoro-2,6-dimethyl-phenyl)-acetonitrile as colourless solid

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

Procedure: A solution of 1.86 g (9 mmol) 2,6-dimethyl-4-fluoro-benzyl bromide and 0.420 g (9 mmol) sodium cyanide in 21 ml ethanol/water 6:1 was heated to reflux for 4h. The cooled reaction mixture was concentrated and extracted with ethyl acetate. The combined extracts were washed with brine, dried over Na2SO4, filtered and evaporated. Filtration of the residue through a silica gel pad with heptane/ethyl acetate 1:1 provided (4-fluoro-2,6-dimethyl-phenyl)-acetonitrile as colourless solid: MS (EI): 163.1 (M+.), 148.1 ((M-CH3)+.), 136.1 ((M-HCN)+., 100%). to reflux for 4h The cooled reaction mixture was concentrated extracted with ethyl acetate The combined extracts were washed with brine dried over Na2SO4 filtered evaporated Filtration of the residue through a silica gel pad with heptane/ethyl acetate 1:1 provided (4-fluoro-2,6-dimethyl-phenyl)-acetonitrile as colourless solid

Conditions: temp:200.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1.30 g (8 mmol) (4-fluoro-2,6-dimethyl-phenyl)-acetonitrile, 3.83 g (4.27 ml, 64 mmol) ethylene diamine and 0.128 g (4 mmol) sulfur in a pressurized glass tube was heated under microwave irradiation to 200° C. for 20 min. The cooled reaction mixture was poured onto water, extracted with methylene chloride, the combined extracts washed with brine, dried over Na2SO4, filtered and evaporated. Purification of the residue by flash-chromatography over silica gel with a ethyl acetate/methanol gradient containing 1% conc. ammonia provided 2-(4-fluoro-2,6-dimethyl-benzyl)-4,5-dihydro-1H-imidazole as light yellow solid: MS (EI): 206.1 ((M+.), 100%). The cooled reaction mixture was poured onto water extracted with methylene chloride the combined extracts washed with brine dried over Na2SO4 filtered evaporated Purification of the residue by flash-chromatography over silica gel with a ethyl acetate/methanol gradient containing 1% conc. ammonia

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

Procedure: A solution of 1.86 g (9 mmol) 2,6-dimethyl-4-fluoro-benzyl bromide and 0.420 g (9 mmol) sodium cyanide in 21 ml ethanol/water 6:1 was heated to reflux for 4h. The cooled reaction mixture was concentrated and extracted with ethyl acetate. The combined extracts were washed with brine, dried over Na2SO4, filtered and evaporated. Filtration of the residue through a silica gel pad with heptane/ethyl acetate 1:1 provided (4-fluoro-2,6-dimethyl-phenyl)-acetonitrile as colourless solid: MS (EI): 163.1 (M+.), 148.1 ((M-CH3)+.), 136.1 ((M-HCN)+., 100%). to reflux for 4h The cooled reaction mixture was concentrated extracted with ethyl acetate The combined extracts were washed with brine dried over Na2SO4 filtered evaporated Filtration of the residue through a silica gel pad with heptane/ethyl acetate 1:1 provided (4-fluoro-2,6-dimethyl-phenyl)-acetonitrile as colourless solid

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:200.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1.30 g (8 mmol) (4-fluoro-2,6-dimethyl-phenyl)-acetonitrile, 3.83 g (4.27 ml, 64 mmol) ethylene diamine and 0.128 g (4 mmol) sulfur in a pressurized glass tube was heated under microwave irradiation to 200° C. for 20 min. The cooled reaction mixture was poured onto water, extracted with methylene chloride, the combined extracts washed with brine, dried over Na2SO4, filtered and evaporated. Purification of the residue by flash-chromatography over silica gel with a ethyl acetate/methanol gradient containing 1% conc. ammonia provided 2-(4-fluoro-2,6-dimethyl-benzyl)-4,5-dihydro-1H-imidazole as light yellow solid: MS (EI): 206.1 ((M+.), 100%). The cooled reaction mixture was poured onto water extracted with methylene chloride the combined extracts washed with brine dried over Na2SO4 filtered evaporated Purification of the residue by flash-chromatography over silica gel with a ethyl acetate/methanol gradient containing 1% conc. ammonia

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

Procedure: A solution of 1.86 g (9 mmol) 2,6-dimethyl-4-fluoro-benzyl bromide and 0.420 g (9 mmol) sodium cyanide in 21 ml ethanol/water 6:1 was heated to reflux for 4h. The cooled reaction mixture was concentrated and extracted with ethyl acetate. The combined extracts were washed with brine, dried over Na2SO4, filtered and evaporated. Filtration of the residue through a silica gel pad with heptane/ethyl acetate 1:1 provided (4-fluoro-2,6-dimethyl-phenyl)-acetonitrile as colourless solid: MS (EI): 163.1 (M+.), 148.1 ((M-CH3)+.), 136.1 ((M-HCN)+., 100%). to reflux for 4h The cooled reaction mixture was concentrated extracted with ethyl acetate The combined extracts were washed with brine dried over Na2SO4 filtered evaporated Filtration of the residue through a silica gel pad with heptane/ethyl acetate 1:1 provided (4-fluoro-2,6-dimethyl-phenyl)-acetonitrile as colourless solid