(4-bromo-2-ethylphenyl)methanamine

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

Procedure: To 4-bromo-2-ethyl-benzylamine (700 mg, 3.3 mmol) and triethylamine (600 μL, 4.3 mmol) in dichloromethane (5 mL) at room temperature was added acetyl chloride (310 μL, 4.5 mmol). The solution was stirred for 1 h, diluted in water and extracted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate, then saturated sodium chloride, dried (Na2SO4), filtered, and concentrated in vacuo to an off-white solid (820 mg, 97%). 1H NMR (300 MHz, CDCl3): δ 1.20 (t, J=7.54 Hz, 3 H) 2.00 (s, 3 H) 2.62 (q, J=7.54 Hz, 2 H) 4.38 (d, J=5.46 Hz, 2 H) 5.59 (s, 1 H) 7.09 (d, J=8.10 Hz, 1 H) 7.26–7.31 (m, 1 H) 7.34 (d, J=1.88 Hz, 1 H). extracted with ethyl acetate The organic layer was washed with saturated sodium bicarbonate saturated sodium chloride, dried (Na2SO4) filtered concentrated in vacuo to an off-white solid (820 mg, 97%)

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

Procedure: To 4-bromo-2-ethyl-benzylamine (700 mg, 3.3 mmol) and triethylamine (600 μL, 4.3 mmol) in dichloromethane (5 mL) at room temperature was added acetyl chloride (310 μL, 4.5 mmol). The solution was stirred for 1 h, diluted in water and extracted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate, then saturated sodium chloride, dried (Na2SO4), filtered, and concentrated in vacuo to an off-white solid (820 mg, 97%). 1H NMR (300 MHz, CDCl3): δ 1.20 (t, J=7.54 Hz, 3 H) 2.00 (s, 3 H) 2.62 (q, J=7.54 Hz, 2 H) 4.38 (d, J=5.46 Hz, 2 H) 5.59 (s, 1 H) 7.09 (d, J=8.10 Hz, 1 H) 7.26–7.31 (m, 1 H) 7.34 (d, J=1.88 Hz, 1 H). extracted with ethyl acetate The organic layer was washed with saturated sodium bicarbonate saturated sodium chloride, dried (Na2SO4) filtered concentrated in vacuo to an off-white solid (820 mg, 97%)

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

Procedure: 2-(4-Bromo-2-ethyl-benzyl)-isoindole-1,3-dione (4 g, 11.7 mmol) and hydrazine (1.8 mL, 58.3 mmol) in chloroform:ethanol (1:1.5, 250 mL) were refluxed for 4 h. The mixture was cooled to room temperature and filtered through a pad of celite. The solution was diluted in water and partitioned. The organic layer was washed with water, saturated sodium bicarbonate, then saturated sodium chloride, dried (Na2SO4), filtered, and then concentrated in vacuo to a yellow oil (2.2 g, 88%). 1H NMR (300 MHz, CDCl3): δ ppm 1.23 (t, J=7.54 Hz, 3 H) 1.65 (s, 2 H) 2.66 (q, J=7.60 Hz, 2 H) 3.84 (s, 2 H) 7.19–7.23 (m, 1 H) 7.30–7.34 (m, 2 H). filtered through a pad of celite The solution was diluted in water partitioned The organic layer was washed with water, saturated sodium bicarbonate saturated sodium chloride, dried (Na2SO4) filtered concentrated in vacuo to a yellow oil (2.2 g, 88%)

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

Procedure: To 4-bromo-2-ethyl-benzylamine (650 mg, 3 mmol) and triethylamine (500 μL, 3.6 mmol) in dichloromethane (5 mL) at room temperature was added methanesulfonyl chloride (283 μL, 3.6 mmol). The solution was stirred 1 h, diluted in water and extracted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate, then saturated sodium chloride, dried (Na2SO4), filtered, and concentrated in vacuo to an off-white solid (880 mg, 100%). 1H NMR (300 MHz, CDCl3): δ ppm 1.25 (t, J=7.54 Hz, 3 H) 2.69 (q, J=7.54 Hz, 2 H) 2.90 (s, 3 H) 4.27–4.31 (m, 2 H) 4.40–4.50 (m, 1 H) 7.21 (d, J=8.10 Hz, 1 H) 7.32–7.40 (m, 2 H). extracted with ethyl acetate The organic layer was washed with saturated sodium bicarbonate saturated sodium chloride, dried (Na2SO4) filtered concentrated in vacuo to an off-white solid (880 mg, 100%)

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

Procedure: To 4-bromo-2-ethyl-benzylamine (650 mg, 3 mmol) and triethylamine (500 μL, 3.6 mmol) in dichloromethane (5 mL) at room temperature was added methanesulfonyl chloride (283 μL, 3.6 mmol). The solution was stirred 1 h, diluted in water and extracted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate, then saturated sodium chloride, dried (Na2SO4), filtered, and concentrated in vacuo to an off-white solid (880 mg, 100%). 1H NMR (300 MHz, CDCl3): δ ppm 1.25 (t, J=7.54 Hz, 3 H) 2.69 (q, J=7.54 Hz, 2 H) 2.90 (s, 3 H) 4.27–4.31 (m, 2 H) 4.40–4.50 (m, 1 H) 7.21 (d, J=8.10 Hz, 1 H) 7.32–7.40 (m, 2 H). extracted with ethyl acetate The organic layer was washed with saturated sodium bicarbonate saturated sodium chloride, dried (Na2SO4) filtered concentrated in vacuo to an off-white solid (880 mg, 100%)

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

Procedure: To 4-bromo-2-ethyl-benzylamine (700 mg, 3.3 mmol) and triethylamine (600 μL, 4.3 mmol) in dichloromethane (5 mL) at room temperature was added acetyl chloride (310 μL, 4.5 mmol). The solution was stirred for 1 h, diluted in water and extracted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate, then saturated sodium chloride, dried (Na2SO4), filtered, and concentrated in vacuo to an off-white solid (820 mg, 97%). 1H NMR (300 MHz, CDCl3): δ 1.20 (t, J=7.54 Hz, 3 H) 2.00 (s, 3 H) 2.62 (q, J=7.54 Hz, 2 H) 4.38 (d, J=5.46 Hz, 2 H) 5.59 (s, 1 H) 7.09 (d, J=8.10 Hz, 1 H) 7.26-7.31 (m, 1 H) 7.34 (d, J=1.88 Hz, 1 H). extracted with ethyl acetate The organic layer was washed with saturated sodium bicarbonate saturated sodium chloride, dried (Na2SO4) filtered concentrated in vacuo to an off-white solid (820 mg, 97%)

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

Procedure: 2-(4-Bromo-2-ethyl-benzyl)-isoindole-1,3-dione (4 g, 11.7 mmol) and hydrazine (1.8 mL, 58.3 mmol) in chloroform:ethanol (1:1.5, 250 mL) were refluxed for 4 h. The mixture was cooled to room temperature and filtered through a pad of celite. The solution was diluted in water and partitioned. The organic layer was washed with water, saturated sodium bicarbonate, then saturated sodium chloride, dried (Na2SO4), filtered, and then concentrated in vacuo to a yellow oil (2.2 g, 88%). 1H NMR (300 MHz, CDCl3): δ ppm 1.23 (t, J=7.54 Hz, 3 H) 1.65 (s, 2 H) 2.66 (q, J=7.60 Hz, 2 H) 3.84 (s, 2 H) 7.19-7.23 (m, 1 H) 7.30-7.34 (m, 2 H). filtered through a pad of celite The solution was diluted in water partitioned The organic layer was washed with water, saturated sodium bicarbonate saturated sodium chloride, dried (Na2SO4) filtered concentrated in vacuo to a yellow oil (2.2 g, 88%)

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

Procedure: To 4-bromo-2-ethyl-benzylamine (650 mg, 3 mmol) and triethylamine (500 μL, 3.6 mmol) in dichloromethane (5 mL) at room temperature was added methanesulfonyl chloride (283 μL, 3.6 mmol). The solution was stirred 1 h, diluted in water and extracted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate, then saturated sodium chloride, dried (Na2SO4), filtered, and concentrated in vacuo to an off-white solid (880 mg, 100%). 1H NMR (300 MHz, CDCl3): δ ppm 1.25 (t, J=7.54 Hz, 3 H) 2.69 (q, J=7.54 Hz, 2 H) 2.90 (s, 3 H) 4.27-4.31 (m, 2H) 4.40-4.50 (m, 1 H) 7.21 (d, J=8.10 Hz, 1 H) 7.32-7.40 (m, 2 H). extracted with ethyl acetate The organic layer was washed with saturated sodium bicarbonate saturated sodium chloride, dried (Na2SO4) filtered concentrated in vacuo to an off-white solid (880 mg, 100%)

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

Procedure: To 4-bromo-2-ethyl-benzylamine (700 mg, 3.3 mmol) and triethylamine (600 μL, 4.3 mmol) in dichloromethane (5 mL) at room temperature was added acetyl chloride (310 μL, 4.5 mmol). The solution was stirred for 1 h, diluted in water and extracted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate, then saturated sodium chloride, dried (Na2SO4), filtered, and concentrated in vacuo to an off-white solid (820 mg, 97%). 1H NMR (300 MHz, CDCl3): δ 1.20 (t, J=7.54 Hz, 3H) 2.00 (s, 3H) 2.62 (q, J=7.54 Hz, 2H) 4.38 (d, J=5.46 Hz, 2H) 5.59 (s, 1H) 7.09 (d, J=8.10 Hz, 1H) 7.26-7.31 (m, 1H) 7.34 (d, J=1.88 Hz, 1H). extracted with ethyl acetate The organic layer was washed with saturated sodium bicarbonate saturated sodium chloride, dried (Na2SO4) filtered concentrated in vacuo to an off-white solid (820 mg, 97%)

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

Procedure: 2-(4-Bromo-2-ethyl-benzyl)-isoindole-1,3-dione (4 g, 11.7 mmol) and hydrazine (1.8 mL, 58.3 mmol) in chloroform:ethanol (1:1.5, 250 mL) were refluxed for 4 h. The mixture was cooled to room temperature and filtered through a pad of celite. The solution was diluted in water and partitioned. The organic layer was washed with water, saturated sodium bicarbonate, then saturated sodium chloride, dried (Na2SO4), filtered, and then concentrated in vacuo to a yellow oil (2.2 g, 88%). 1H NMR (300 MHz, CDCl3): δ ppm 1.23 (t, J=7.54 Hz, 3H) 1.65 (s, 2H) 2.66 (q, J=7.60 Hz, 2H) 3.84 (s, 2H) 7.19-7.23 (m, 1H) 7.30-7.34 (m, 2H). filtered through a pad of celite The solution was diluted in water partitioned The organic layer was washed with water, saturated sodium bicarbonate saturated sodium chloride, dried (Na2SO4) filtered concentrated in vacuo to a yellow oil (2.2 g, 88%)

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

Procedure: To 4-bromo-2-ethyl-benzylamine (650 mg, 3 mmol) and triethylamine (500 μL, 3.6 mmol) in dichloromethane (5 mL) at room temperature was added methanesulfonyl chloride (283 μL, 3.6 mmol). The solution was stirred 1 h, diluted in water and extracted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate, then saturated sodium chloride, dried (Na2SO4), filtered, and concentrated in vacuo to an off-white solid (880 mg, 100%). 1H NMR (300 MHz, CDCl3): δ ppm 1.25 (t, J=7.54 Hz, 3H) 2.69 (q, J=7.54 Hz, 2H) 2.90 (s, 3H) 4.27-4.31 (m, 2H) 4.40-4.50 (m, 1H) 7.21 (d, J=8.10 Hz, 1H) 7.32-7.40 (m, 2H). extracted with ethyl acetate The organic layer was washed with saturated sodium bicarbonate saturated sodium chloride, dried (Na2SO4) filtered concentrated in vacuo to an off-white solid (880 mg, 100%)

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

Procedure: To 4-bromo-2-ethyl-benzylamine (700 mg, 3.3 mmol) and triethylamine (600 μL, 4.3 mmol) in dichloromethane (5 mL) at room temperature was added acetyl chloride (310 μL, 4.5 mmol). The solution was stirred for 1 h, diluted in water and extracted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate, then saturated sodium chloride, dried (Na2SO4), filtered, and concentrated in vacuo to an off-white solid (820 mg, 97%). 1H NMR (300 MHz, CDCl3): δ 1.20 (t, J=7.54 Hz, 3 H) 2.00 (s, 3 H) 2.62 (q, J=7.54 Hz, 2 H) 4.38 (d, J=5.46 Hz, 2 H) 5.59 (s, 1 H) 7.09 (d, J=8.10 Hz, 1 H) 7.26–7.31 (m, 1 H) 7.34 (d, J=1.88 Hz, 1 H). extracted with ethyl acetate The organic layer was washed with saturated sodium bicarbonate saturated sodium chloride, dried (Na2SO4) filtered concentrated in vacuo to an off-white solid (820 mg, 97%)