2-(3-Iodo-propyl)-isoindole-1,3-dione

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

Procedure: A solution of 10.0 g (0.04 mol) of N-(3-bromopropyl)-phthalimide in 240 mL of acetone was treated with 41.7 g (0.25 mol) of potassium iodide and stirred at room temperature for 4 days. The reaction mixture was filtered and the filtrate was diluted with 800 mL of ether and filtered again through celite. The filtrate was then concentrated at reduced pressure. The resulting yellow solid was recrystallized from 550 mL of hexane (filtered hot and boiled down to 300 mL) to yield 10.71 g (91.1%) of 2 as off-white needles. The reaction mixture was filtered the filtrate was diluted with 800 mL of ether filtered again through celite The filtrate was then concentrated at reduced pressure The resulting yellow solid was recrystallized from 550 mL of hexane (filtered hot and boiled down to 300 mL)

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

Procedure: A solution of 10.0 g (0.04 mol) of N-(3-bromopropyl)phthalimide in 240 mL of acetone was treated with 41.7 g (0.25 mol) of potassium iodide and stirred at room temperature for 4 days. The reaction mixture was filtered and the filtrate was diluted with 800 mL of ether and filtered again through celite. The filtrate was then concentrated at reduced pressure. The resulting yellow solid was recrystallized from 550 mL of hexane (filtered hot and boiled down to 300 mL) to yield 10.71 g (91.1%) of 2 as off-white needles. The reaction mixture was filtered the filtrate was diluted with 800 mL of ether filtered again through celite The filtrate was then concentrated at reduced pressure The resulting yellow solid was recrystallized from 550 mL of hexane (filtered hot and boiled down to 300 mL)

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

Procedure: A solution of 10.0 g (0.04 mol) of N-(3-bromopropyl)phthalimide in 240 mL of acetone was treated with 41.7 g (0.25 mol) of potassium iodide and stirred at room temperature for 4 days. The reaction mixture was filtered and the filtrate was diluted with 800 mL of ether and filtered again through celite. The filtrate was then concentrated at reduced pressure. The resulting yellow solid was recrystallized from 550 mL of hexane (filtered hot and boiled down to 300 mL) to yield 10.71 g (91.1%) of 2 as off-white needles. The reaction mixture was filtered the filtrate was diluted with 800 mL of ether filtered again through celite The filtrate was then concentrated at reduced pressure The resulting yellow solid was recrystallized from 550 mL of hexane (filtered hot and boiled down to 300 mL)

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

Procedure: A solution of 50.0 g (0.187 mol) of N-(3-bromopropyl)phthalimide in 1.2 L of acetone was treated with 208.5 g of potassium iodide and stirred at room temperature for 4 days. The reaction was filtered and the filtrate was diluted with 4 L of ether. This was then filtered through CELITE. The filtrate was concentrated under reduced pressure to a yellow solid. This was recrystallized from hexane to yield 46.5 g (79%) of off-white solid. The reaction was filtered the filtrate was diluted with 4 L of ether This was then filtered through CELITE The filtrate was concentrated under reduced pressure to a yellow solid This was recrystallized from hexane

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

Procedure: A solution of 50.0 g (0.187 mol) of N-(3-bromopropyl)phthalimide in 1.2 L of acetone was treated with 208.5 g of potassium iodide and stirred at room temperature for 4 days. The reaction was filtered and the filtrate was diluted with 4 L of ether. This was then filtered through CELITE. The filtrate was concentrated under reduced pressure to a yellow solid. This was recrystallized from hexane to yield 46.5 g (79%) of off-white solid. The reaction was filtered the filtrate was diluted with 4 L of ether This was then filtered through CELITE The filtrate was concentrated under reduced pressure to a yellow solid This was recrystallized from hexane

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

Procedure: A solution of 50.0 g (0.187 mol) of N-(3-bromopropyl)phthalimide in 1.2 L of acetone was treated with 208.5 g of potassium iodide and stirred at room temperature for 4 days. The reaction was filtered and the filtrate was diluted with 4 L of ether. This was then filtered through CELITE. The filtrate was concentrated under reduced pressure to a yellow solid. This was recrystallized from hexane to yield 46.5 g (79%) of off-white solid. The reaction was filtered the filtrate was diluted with 4 L of ether This was then filtered through CELITE The filtrate was concentrated under reduced pressure to a yellow solid This was recrystallized from hexane

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

Procedure: Under an atmosphere of nitrogen, a stirred suspension of 1.6 g (24 mg.atom) of zinc dust (<10 micron diameter) in 20 ml of dimethylformamide was treated with 0.11 ml (1.2 mmol) of 1,2-dibromoethane and the mixture was heated to 60° C. then allowed to cool to room temperature. The heating and cooling was repeated twice more. 0.04 ml (0.24 mmol) of chlorotrimethylsilane was added and the mixture stirred at ambient temperature for 30 minutes. The mixture was then treated with 1.26 g (4 mmol) of N-(3-iodopropyl)phthalimide and the resulting suspension stirred for 30 minutes at ambient temperature and then heated at 35° C. for 1 hour and cooled. To the mixture were then added sequentially 750 mg (3 mmol) of 1-iodo-3-nitrobenzene, 60 mg (0.06 mmol) of tris(dibenzylideneacetone)dipalladium and 70 mg (0.23 mmol) of tri(o-tolyl)phosphine and the resulting mixture stirred at ambient temperature for 1 hour. The suspension was filtered and the filtrate diluted with 50 ml of ethyl acetate, washed twice with 40 ml of water, dried over magnesium sulfate, filtered and evaporated. The product was purified by flash chromatography on silica gel using ethyl acetate/isohexane in a ratio of 1:2 as eluent. Product containing fractions were combined and evaporated to give 190 mg (20%) of 2-[3-(3-nitrophenyl)-propyl]-isoindole-1,3-dione as a pale pink solid. [Mass spectrum (ESI) MH+ =311]. to cool to room temperature The heating and cooling the resulting suspension stirred for 30 minutes at ambient temperature heated at 35° C. for 1 hour cooled the resulting mixture stirred at ambient temperature for 1 hour The suspension was filtered the filtrate diluted with 50 ml of ethyl acetate washed twice with 40 ml of water dried over magnesium sulfate filtered evaporated The product was purified by flash chromatography on silica gel Product containing fractions evaporated

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

Procedure: To a solution of 15 g (100 mmol) of sodium iodide in 120 ml of acetone was added 3 g (11 mmol) of N-(3-bromopropyl)phthalimide and the mixture was heated at reflux for 30 minutes. The cooled mixture was filtered and evaporated. The residue was partitioned between 50 ml of diethyl ether and 50 ml of water. The organic phase was dried over magnesium sulfate, filtered and evaporated to give 2.6 g (75%) of N-(3-iodopropyl)phthalimide as a white solid. [Mass spectrum (ESI) MH+ =316]. the mixture was heated at reflux for 30 minutes The cooled mixture was filtered evaporated The residue was partitioned between 50 ml of diethyl ether and 50 ml of water The organic phase was dried over magnesium sulfate filtered evaporated

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

Procedure: A solution of 50.0 g (0.187 mol) of N-(3-bromopropyl)phthalimide in 1.2 L of acetone was treated with 208.5 g of potassium iodide and stirred at room temperature for 4 days. The reaction was filtered and the filtrate was diluted with 4 L of ether. This was then filtered through CELITE. The filtrate was concentrated under reduced pressure to a yellow solid. This was recrystallized from hexane to yield 46.5 g (79%) of off-white solid. The reaction was filtered the filtrate was diluted with 4 L of ether This was then filtered through CELITE The filtrate was concentrated under reduced pressure to a yellow solid This was recrystallized from hexane

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

Procedure: A solution of 10.0 g (0.04 mol) of N-(3-bromopropyl)-phthalimide in 240 mL of acetone was treated with 41.7 g (0.25 mol) of potassium iodide and stirred at room temperature for 4 days. The reaction mixture was filtered and the filtrate was diluted with 800 mL of ether and filtered again through celite. The filtrate was then concentrated at reduced pressure. The resulting yellow solid was recrystallized from 550 mL of hexane (filtered hot and boiled down to 300 mL) to yield 10.71 g (91.1%) of 2 as off-white needles. The reaction mixture was filtered the filtrate was diluted with 800 mL of ether filtered again through celite The filtrate was then concentrated at reduced pressure The resulting yellow solid was recrystallized from 550 mL of hexane (filtered hot and boiled down to 300 mL)

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

Procedure: A solution of 10.0 g (0.04 mol) of N-(3-bromopropyl)phthalimide in 240 mL of acetone was treated with 41.7 g (0.25 mol) of potassium iodide and stirred at room temperature for 4 days. The reaction mixture was filtered and the filtrate was diluted with 800 mL of ether and filtered again through celite. The filtrate was then concentrated at reduced pressure. The resulting yellow solid was recrystallized from 550 mL of hexane (filtered hot and boiled down to 300 mL) to yield 10.71 g (91.1%) of 2 as off-white needles. The reaction mixture was filtered the filtrate was diluted with 800 mL of ether filtered again through celite The filtrate was then concentrated at reduced pressure The resulting yellow solid was recrystallized from 550 mL of hexane (filtered hot and boiled down to 300 mL)

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

Procedure: A solution of 50.0 g (0.187 mol) of N-(3-bromopropyl)phthalimide in 1.2 L of acetone was treated with 208.5 g of potassium iodide and stirred at room temperature for 4 days. The reaction was filtered and the filtrate was diluted with 4 L of ether. This was then filtered through CELITE. The filtrate was concentrated under reduced pressure to a yellow solid. This was recrystallized from hexane to yield 46.5 g (79%) of off-white solid. The reaction was filtered the filtrate was diluted with 4 L of ether This was then filtered through CELITE The filtrate was concentrated under reduced pressure to a yellow solid This was recrystallized from hexane