1-iodo-4-(2-methoxyethoxy)benzene

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

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

Procedure: A mixture of 4-iodophenol (1.0 g) 1-bromo-2-methoxyethane (0.7 g), potassium iodide (0.83 g), potassium carbonate (0.7 g) and methyl isobutylketone (10 ml) was refluxed for 18 h, diluted with ER (50 ml), filtered and evaporated. The residue was distilled to give the title compound (0.83 g). T.l.c. (cyclohexane-ER 1:1) Rf 0.6 was refluxed for 18 h diluted with ER (50 ml) filtered evaporated The residue was distilled

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

Procedure: A mixture of 4-iodophenol (20 g), 2-bromoethylmethyl ether (11.4 g), potassium carbonate (12.5 g) and dimethylformamide (100 ml) was stirred at 80° C. for 4 hours. A further portion of 2-bromoethylmethyl ether (2.24 g) and potassium carbonate (2.5 g) was then added and the mixture stirred at 80° C. for a further 1 hour. The dimethylformamide was removed by evaporation. The residue was treated with a 2M aqueous sodium hydroxide solution (50 ml) and the mixture extracted with diethyl ether (3×50 ml). The ethereal extracts were combined, washed with 2M aqueous sodium hydroxide solution (2×20 ml), brine (20 ml), dried (MgSO4) and evaporated to give 4-(2-methoxyethoxy)iodobenzene (23 g) as a white solid, m.p. 36-37° C. NMR ([CD3 ]2SO): 3.3 (3H, s), 3.6-3.7 (2H, m), 4.0-4.1 (2H, m), 6.72-6.82 (2H, d) and 7.52-7.62 (2H, d). the mixture stirred at 80° C. for a further 1 hour The dimethylformamide was removed by evaporation The residue was treated with a 2M aqueous sodium hydroxide solution (50 ml) the mixture extracted with diethyl ether (3×50 ml) washed with 2M aqueous sodium hydroxide solution (2×20 ml), brine (20 ml) dried (MgSO4) evaporated

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

Procedure: A mixture of 4-iodophenol (20 g), 2-bromoethylmethyl ether (11.4 g), potassium carbonate (12.5 g) and dimethylformamide (100 ml) was stirred at 80° C. for 4 hours. A further portion of 2-bromoethylmethyl ether (2.24 g) and potassium carbonate (2.5 g) was then added and the mixture stirred at 80° C. for a further 1 hour. The dimethylformamide was removed by evaporation. The residue was treated with a 2M aqueous sodium hydroxide solution (50 ml) and the mixture extracted with diethyl ether (3×50 ml). The ethereal extracts were combined, washed with 2M aqueous sodium hydroxide solution (2×20 ml), brine (20 ml), dried (MgSO4) and evaporated to give 4-(2-methoxyethoxy)iodobenzene (23 g) as a white solid, m.p. 36-37° C. NMR ([CD3 ]2SO): 3.3 (3H, s), 3.6-3.7 (2H, m), 4.0-4.1 (2H, m), 6.72-6.82 (2H, d) and 7.52-7.62 (2H, d). the mixture stirred at 80° C. for a further 1 hour The dimethylformamide was removed by evaporation The residue was treated with a 2M aqueous sodium hydroxide solution (50 ml) the mixture extracted with diethyl ether (3×50 ml) washed with 2M aqueous sodium hydroxide solution (2×20 ml), brine (20 ml) dried (MgSO4) evaporated

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

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

Procedure: Triphenylphosphine (2.8 g, 10.7 mmol) was added to an ice-cold solution of 4-iodophenol (2.2 g, 10.0 mmol) and 2-methoxyethanol (0.79 ml, 10.0 mmol) in tetrahydrofuran (10 ml). A solution of diethyl azodicarboxylate (1.88 ml, 11.5 mmol) in tetrahydrofuran (10 ml) was then added dropwise, and the reaction stirred at room temperature for 18 hours. The mixture was evaporated under reduced pressure, the residue partitioned between dichloromethane and hydrochloric acid (2N) and the phases separated. The organic layer was washed with brine, dried (MgSO4) and evaporated under reduced pressure. The residue was triturated with diethyl ether, the resulting suspension filtered and the filtrate concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel using pentane:dichloromethane (75:25) as eluant to give the title compound, (2.0 g, 71%) as an oil. The mixture was evaporated under reduced pressure the residue partitioned between dichloromethane and hydrochloric acid (2N) the phases separated The organic layer was washed with brine dried (MgSO4) evaporated under reduced pressure The residue was triturated with diethyl ether the resulting suspension filtered the filtrate concentrated under reduced pressure The crude product was purified by column chromatography on silica gel

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

Procedure: Triphenylphosphine (2.8 g, 10.7 mmol) was added to an ice-cold solution of 4-iodophenol (2.2 g, 10.0 mmol) and 2-methoxyethanol (0.79 ml, 10.0 mmol) in tetrahydrofuran (10 ml). A solution of diethyl azodicarboxylate (1.88 ml, 11.5 mmol) in tetrahydrofuran (10 ml) was then added dropwise, and the reaction stirred at room temperature for 18 hours. The mixture was evaporated under reduced pressure, the residue partitioned between dichloromethane and hydrochloric acid (2N) and the phases separated. The organic layer was washed with brine, dried (MgSO4) and evaporated under reduced pressure. The residue was triturated with diethyl ether, the resulting suspension filtered and the filtrate concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel using pentane:dichloromethane (75:25) as eluant to give the title compound, (2.0 g, 71%) as an oil. The mixture was evaporated under reduced pressure the residue partitioned between dichloromethane and hydrochloric acid (2N) the phases separated The organic layer was washed with brine dried (MgSO4) evaporated under reduced pressure The residue was triturated with diethyl ether the resulting suspension filtered the filtrate concentrated under reduced pressure The crude product was purified by column chromatography on silica gel

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

Procedure: A mixture of 4-iodophenol (1.0 g) 1-bromo-2-methoxyethane (0.7 g), potassium iodide (0.83 g), potassium carbonate (0.7 g) and methyl isobutylketone (10 ml) was refluxed for 18 h, diluted with ER (50 ml), filtered and evaporated. The residue was distilled to give the title compound (0.83 g). T.l.c. (cyclohexane-ER 1:1) Rf 0.6 was refluxed for 18 h diluted with ER (50 ml) filtered evaporated The residue was distilled

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

Procedure: A mixture of 4-iodophenol (20 g), 2-bromoethylmethyl ether (11.4 g), potassium carbonate (12.5 g) and dimethylformamide (100 ml) was stirred at 80° C. for 4 hours. A further portion of 2-bromoethylmethyl ether (2.24 g) and potassium carbonate (2.5 g) was then added and the mixture stirred at 80° C. for a further 1 hour. The dimethylformamide was removed by evaporation. The residue was treated with a 2M aqueous sodium hydroxide solution (50 ml) and the mixture extracted with diethyl ether (3×50 ml). The ethereal extracts were combined, washed with 2M aqueous sodium hydroxide solution (2×20 ml), brine (20 ml), dried (MgSO4) and evaporated to give 4-(2-methoxyethoxy)iodobenzene (23 g) as a white solid, m.p. 36-37° C. NMR ([CD3 ]2SO): 3.3 (3H, s), 3.6-3.7 (2H, m), 4.0-4.1 (2H, m), 6.72-6.82 (2H, d) and 7.52-7.62 (2H, d). the mixture stirred at 80° C. for a further 1 hour The dimethylformamide was removed by evaporation The residue was treated with a 2M aqueous sodium hydroxide solution (50 ml) the mixture extracted with diethyl ether (3×50 ml) washed with 2M aqueous sodium hydroxide solution (2×20 ml), brine (20 ml) dried (MgSO4) evaporated