1,3,5-tris(bromomethyl)benzene

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

Procedure: To a solution of 5 g (0.014 mole) of the tribromide 8 in 100 ml of CH3CN was added, at room temperature and under argon atmosphere, in a dropwise fashion 3.72 g (0.028 mole) of nitronium tetrafluoroborate in 200 ml of CH3CN. The solution was then stirred for 20 minutes longer, poured into water and the mixture extracted with CH2Cl2. The CH2Cl2 extracts were washed with 10% NaHCO3, dried (Na2SO4) and solvents removed to afford 4.86 g (86%) of the desired nitro compound 27: NMR (CDCl3) 4.5 (s,6,--CH2Br), 7.55 (s,--C6H2). the mixture extracted with CH2Cl2 The CH2Cl2 extracts were washed with 10% NaHCO3 dried (Na2SO4) and solvents removed

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

Procedure: To a solution of 5 g (0.014 mole) of the tribromide 8 in 100 ml of CH3CN was added, at room temperature and under argon atmosphere, in a dropwise fashion 3.72 g (0.028 mole) of nitronium tetrafluoroborate in 200 ml of CH3CN. The solution was then stirred for 20 minutes longer, poured into water and the mixture extracted with CH2Cl2. The CH2Cl2 extracts were washed with 10% NaHCO3, dried (Na2SO4) and solvents removed to afford 4.86 g (86%) of the desired nitro compound 27: NMR (CDCl3) 4.5 (s,6,--CH2Br), 7.55 (s,--C6H2). the mixture extracted with CH2Cl2 The CH2Cl2 extracts were washed with 10% NaHCO3 dried (Na2SO4) and solvents removed

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

Procedure: To a solution of 5 g (0.014 mole) of the tribromide 8 in 100 ml of CH3CN was added, at room temperature and under argon atmosphere, in a dropwise fashion 3.72 g (0.028 mole) of nitronium tetrafluoroborate in 200 ml of CH3CN. The solution was then stirred for 20 minutes longer, poured into water and the mixture extracted with CH2Cl2. The CH2Cl2 extracts were washed with 10% NaHCO3, dried (Na2SO4) and solvents removed to afford 4.86 g (86%) of the desired nitro compound 27: NMR (CDCl3) 4.5 (s,6,--CH2Br), 7.55 (s,--C6H2). the mixture extracted with CH2Cl2 The CH2Cl2 extracts were washed with 10% NaHCO3 dried (Na2SO4) and solvents removed

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

Procedure: To a solution of 5 g (0.014 mole) of the tribromide 8 in 100 ml of CH3CN was added, at room temperature and under argon atmosphere, in a dropwise fashion 3.72 g (0.028 mole) of nitronium tetrafluoroborate in 200 ml of CH3CN. The solution was then stirred for 20 minutes longer, poured into water and the mixture extracted with CH2Cl2. The CH2Cl2 extracts were washed with 10% NaHCO3, dried (Na2SO4) and solvents removed to afford 4.86 g (86%) of the desired nitro compound 27: NMR (CDCl3) 4.5 (s,6,--CH2Br), 7.55 (s,--C6H2). the mixture extracted with CH2Cl2 The CH2Cl2 extracts were washed with 10% NaHCO3 dried (Na2SO4) and solvents removed

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

Procedure: 4,5-dichloroimidazole (3.00 g, 21.90 mmol) was dissolved in THF and brought to reflux. Potassium hydroxide (2.46 g, 43.80 mmol) was added to the solution and allowed to reflux for 30 min. 1,3,5-tris(bromomethyl)benzene (2.61, 7.30 mmol) was added to the solution and refluxed overnight. Solution was filtered while hot to remove the KBr precipitate and the filtrate returned to reflux. 1-(bromomethyl)naphthalene (4.84 g, 21.90 mmol) was added to the solution and refluxed for 3 h. The volatiles were removed in vacuo and the resulting waxy yellow solid was washed in ethyl ether. A resulting product will be collected and analyzed. to reflux to reflux for 30 min refluxed overnight Solution was filtered while hot to remove the KBr precipitate to reflux refluxed for 3 h The volatiles were removed in vacuo the resulting waxy yellow solid was washed in ethyl ether A resulting product will be collected

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

Procedure: 4,5-dichloroimidazole (3.00 g, 21.90 mmol) was dissolved in THF and brought to reflux. Potassium hydroxide (2.46 g, 43.80 mmol) was added to the solution and allowed to reflux for 30 min. 2-(bromoethyl)naphthalene (5.15 g, 21.90 mmol) was added to the solution and refluxed for 3 h. Solution was filtered while hot to remove the KBr precipitate and the filtrate was returned to reflux. 1,3,5-tris(bromomethyl)benzene (2.61, 7.30 mmol) was added to the solution and refluxed overnight. The volatiles were removed in vacuo and the resulting waxy yellow solid was washed in ethyl ether. A resulting product will be collected and analyzed. to reflux to reflux for 30 min refluxed for 3 h Solution was filtered while hot to remove the KBr precipitate to reflux refluxed overnight The volatiles were removed in vacuo the resulting waxy yellow solid was washed in ethyl ether A resulting product will be collected

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

Procedure: 4,5-dichloroimidazole (3.00 g, 21.90 mmol) was dissolved in THF and brought to reflux. Potassium hydroxide (2.46 g, 43.80 mmol) was added to the solution and allowed to reflux for 30 min. 1,3,5-tris(bromomethyl)benzene (2.61, 7.30 mmol) was added to the solution and refluxed overnight. Solution was filtered while hot to remove the KBr precipitate and the filtrate returned to reflux. 2-(bromomethyl)naphthalene (4.84 g, 21.90 mmol) was added to the solution and refluxed for 3 h. The volatiles were removed in vacuo and the resulting waxy yellow solid was washed in ethyl ether. A white precipitate was collected and analyzed. 1H NMR (300 MHz, DMSO-d6): δ 4.87, 5.18, 7.32, 7.57, 7.95, 10.30. to reflux to reflux for 30 min refluxed overnight Solution was filtered while hot to remove the KBr precipitate to reflux refluxed for 3 h The volatiles were removed in vacuo the resulting waxy yellow solid was washed in ethyl ether A white precipitate was collected

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

Procedure: 4,5-dichloroimidazole (3.00 g, 21.90 mmol) was dissolved in THF and brought to reflux. Potassium hydroxide (2.46 g, 43.80 mmol) was added to the solution and allowed to reflux for 30 min. 1,3,5-tris(bromomethyl)benzene (2.61, 7.30 mmol) was added to the solution and refluxed overnight. Solution was filtered while hot to remove the KBr precipitate and the filtrate returned to reflux. 2-(bromomethyl)naphthalene (4.84 g, 21.90 mmol) was added to the solution and refluxed for 3 h. The volatiles were removed in vacuo and the resulting waxy yellow solid was washed in ethyl ether. A white precipitate was collected and analyzed. 1H NMR (300 MHz, DMSO-d6): δ 4.87, 5.18, 7.32, 7.57, 7.95, 10.30. to reflux to reflux for 30 min refluxed overnight Solution was filtered while hot to remove the KBr precipitate to reflux refluxed for 3 h The volatiles were removed in vacuo the resulting waxy yellow solid was washed in ethyl ether A white precipitate was collected

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

Procedure: To a solution of 5 g (0.014 mole) of the tribromide 8 in 100 ml of CH3CN was added, at room temperature and under argon atmosphere, in a dropwise fashion 3.72 g (0.028 mole) of nitronium tetrafluoroborate in 200 ml of CH3CN. The solution was then stirred for 20 minutes longer, poured into water and the mixture extracted with CH2Cl2. The CH2Cl2 extracts were washed with 10% NaHCO3, dried (Na2SO4) and solvents removed to afford 4.86 g (86%) of the desired nitro compound 27: NMR (CDCl3) 4.5 (s,6,--CH2Br), 7.55 (s,--C6H2). the mixture extracted with CH2Cl2 The CH2Cl2 extracts were washed with 10% NaHCO3 dried (Na2SO4) and solvents removed

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

Procedure: To a solution of 5 g (0.014 mole) of the tribromide 8 in 100 ml of CH3CN was added, at room temperature and under argon atmosphere, in a dropwise fashion 3.72 g (0.028 mole) of nitronium tetrafluoroborate in 200 ml of CH3CN. The solution was then stirred for 20 minutes longer, poured into water and the mixture extracted with CH2Cl2. The CH2Cl2 extracts were washed with 10% NaHCO3, dried (Na2SO4) and solvents removed to afford 4.86 g (86%) of the desired nitro compound 27: NMR (CDCl3) 4.5 (s,6,--CH2Br), 7.55 (s,--C6H2). the mixture extracted with CH2Cl2 The CH2Cl2 extracts were washed with 10% NaHCO3 dried (Na2SO4) and solvents removed

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

Procedure: To a suspension of 0.5 g (0.0008 mole) of the amine-hydrochloride 8 in 20 ml of CH2Cl2 was added all at once 1.4 ml (0.01 mole) of Et3N. The mixture was then cooled to 5°-10° C. and 1.4 g (0.0032 mole) of the sulfonyl chloride 39 in 20 ml of CH2Cl2 was slowly added in a dropwise fashion. The reaction was then allowed to stir at room temperature for 30 minutes after which a TLC was taken. Little of the sulfonyl chloride 9 had reacted by TLC so an additional 100 mg of the amine 8 was added and stirring continued overnight. The mixture was then poured into water and extracted with CH2Cl2. The extract was washed with water, dried (Na2SO4) and the solvent removed yielding crude 43. After column chromatography with SiO2 /5%MeOH/CHCl3, 1.55 g (93%) of the desired tetraamide 43 was obtained. The mixture was then cooled to 5°-10° C. was added stirring continued overnight extracted with CH2Cl2 The extract was washed with water dried (Na2SO4) the solvent removed yielding crude 43

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

Procedure: To a solution of 5 g (0.014 mole) of the tribromide 8 in 100 ml of CH3CN was added, at room temperature and under argon atmosphere, in a dropwise fashion 3.72 g (0.028 mole) of nitronium tetrafluoroborate in 200 ml of CH3CN. The solution was then stirred for 20 minutes longer, poured into water and the mixture extracted with CH2Cl2. The CH2Cl2 extracts were washed with 10% NaHCO3, dried (Na2SO4) and solvents removed to afford 4.86 g (86%) of the desired nitro compound 27: NMR (CDCl3) 4.5 (s,6,--CH2Br), 7.55 (s,--C6H2). the mixture extracted with CH2Cl2 The CH2Cl2 extracts were washed with 10% NaHCO3 dried (Na2SO4) and solvents removed