1-iodo-4-propoxybenzene

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A suspension of 4-iodophenol (3 g, 13.64 mmol), 1-bromopropane (1.845 g, 15.00 mmol), and sodium carbonate (7.54 g, 54.5 mmol) in DMF (30 mL) was stirred at 80° C. for 4 hrs. The reaction mixture was diluted with water (250 mL) and extracted with EtOAc (3×75 mL). The combined organic extracts were washed with 0.5M NaOH (2×50 mL), and water (2×50 mL), and then dried over MgSO4. The solvent was removed. The crude product (3.11 g) was obtained, which was directly used for the next reaction without further purification. 1H NMR (400 MHz, chloroform-d) δ 7.61-7.53 (m, 2H), 6.74-6.67 (m, 2H), 3.90 (t, J=6.5 Hz, 2H), 1.88-1.76 (m, 2H), 1.05 (t, J=7.4 Hz, 3H). extracted with EtOAc (3×75 mL) The combined organic extracts were washed with 0.5M NaOH (2×50 mL), and water (2×50 mL) dried over MgSO4 The solvent was removed

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

Procedure: A mixture of 4-iodophenol (6.6 g), 1-iodopropane (5.1 g), anhydrous potassium carbonate (13.8 g) and acetone (100 ml) was stirred at reflux for 6 hours. Two further portions of 1-iodopropane were added after one hour (5.1 g) and two hours (5.1 g). The acetone was removed by evaporation, the residue was treated with water (100 ml) and the mixture extracted with dichloromethane (2×30 ml). The organic extracts were combined, dried (MgSO4) and evaporated. The residue, an oil, was distilled at 150° C. and 0.5 mm pressure (using a Kugelrohr oven) to give 4-n-propoxyiodobenzene as a colourless oil (7.2 g), NMR(CDCl3): 0.9-1.08(3H,t), 1.7-1.9(2H,m), 3.82-3.92(2H,t), 6.62-6.72(2H,d), 7.5-7.6(2H,d); m/z 262 (M). at reflux for 6 hours The acetone was removed by evaporation the residue was treated with water (100 ml) the mixture extracted with dichloromethane (2×30 ml) dried (MgSO4) evaporated The residue, an oil, was distilled at 150° C.

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

Procedure: A mixture of 4-iodophenol (6.6 g), 1-iodopropane (5.1 g), anhydrous potassium carbonate (13.8 g) and acetone (100 ml) was stirred at reflux for 6 hours. Two further portions of 1-iodopropane were added after one hour (5.1 g) and two hours (5.1 g). The acetone was removed by evaporation, the residue was treated with water (100 ml) and the mixture extracted with dichloromethane (2×30 ml). The organic extracts were combined, dried (MgSO4) and evaporated. The residue, an oil, was distilled at 150° C. and 0.5 mm pressure (using a Kugelrohr oven) to give 4-n-propoxyiodobenzene as a colourless oil (7.2 g), NMR(CDCl3): 0.9-1.08(3H,t), 1.7-1.9(2H,m), 3.82-3.92(2H,t), 6.62-6.72(2H,d), 7.5-7.6(2H,d); m/z 262 (M). at reflux for 6 hours The acetone was removed by evaporation the residue was treated with water (100 ml) the mixture extracted with dichloromethane (2×30 ml) dried (MgSO4) evaporated The residue, an oil, was distilled at 150° C.

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A suspension of 4-iodophenol (3 g, 13.64 mmol), 1-bromopropane (1.845 g, 15.00 mmol), and sodium carbonate (7.54 g, 54.5 mmol) in DMF (30 mL) was stirred at 80° C. for 4 hrs. The reaction mixture was diluted with water (250 mL) and extracted with EtOAc (3×75 mL). The combined organic extracts were washed with 0.5M NaOH (2×50 mL), and water (2×50 mL), and then dried over MgSO4. The solvent was removed. The crude product (3.11 g) was obtained, which was directly used for the next reaction without further purification. 1H NMR (400 MHz, chloroform-d) δ 7.61-7.53 (m, 2H), 6.74-6.67 (m, 2H), 3.90 (t, J=6.5 Hz, 2H), 1.88-1.76 (m, 2H), 1.05 (t, J=7.4 Hz, 3H). extracted with EtOAc (3×75 mL) The combined organic extracts were washed with 0.5M NaOH (2×50 mL), and water (2×50 mL) dried over MgSO4 The solvent was removed