1-fluoro-4-(iodomethyl)benzene

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

Procedure: To a suspension of Mg (3 g, 0.123 mol) in THF (40 ml) was added a small amount of solid I2 (20 mg). The mixture was heated to reflux under nitrogen. To the mixture was then added the 2-bromothiophene solution (5 ml) (19.6 g of 2-bromothiophene in 40 ml of THF). After the iodine color disappeared, to the suspension was added the rest of 2-bromothiophene solution dropwise keeping reflux. After the addition, the mixture was heated under reflux for 2 h., then was cooled to room temperature. To this mixture was added 4-fluorobenzyl iodide (or 4-fluorobenzyl bromide) followed by Li2CuCl4 (5 ml) solution keeping the temperature under 40° C. using a cool water bath. The mixture was stirred at room temperature for 2 h. To the mixture was added sat. NH4Cl solution (100 ml), the mixture was stirred for 30 min., the organic layer was separated and washed with 10% sodium thiosulfate solution (50 ml), followed by distilled water (100 ml). The organic layer was then dried over MgSO4 and concentrated to give 19 g of 2-(4-fluorobenzyl)thiophene as an oil. Purification was achieved by vacuum distillation (110° C., 5 mm Hg). The mixture was heated to reflux under nitrogen dropwise keeping reflux After the addition the mixture was heated under reflux for 2 h. under 40° C. the mixture was stirred for 30 min. the organic layer was separated washed with 10% sodium thiosulfate solution (50 ml) by distilled water (100 ml) The organic layer was then dried over MgSO4 concentrated

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

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

Procedure: mp. 151° -153° C., by the reaction of 1-[2,4-dichloro-β-(2,4-dichlorobenzyloxy)phenethyl]-imidazole and p-fluorobenzyl iodide.

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

Procedure: mp. 151° -153° C., by the reaction of 1-[2,4-dichloro-β-(2,4-dichlorobenzyloxy)phenethyl]-imidazole and p-fluorobenzyl iodide.

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

Procedure: mp. 151° -153° C., by the reaction of 1-[2,4-dichloro-β-(2,4-dichlorobenzyloxy)phenethyl]-imidazole and p-fluorobenzyl iodide.

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

Procedure: To a suspension of Mg (3 g, 0.123 mol) in THF (40 ml) was added a small amount of solid I2 (20 mg). The mixture was heated to reflux under nitrogen. To the mixture was then added the 2-bromothiophene solution (5 ml) (19.6 g of 2-bromothiophene in 40 ml of THF). After the iodine color disappeared, to the suspension was added the rest of 2-bromothiophene solution dropwise keeping reflux. After the addition, the mixture was heated under reflux for 2 h., then was cooled to room temperature. To this mixture was added 4-fluorobenzyl iodide (or 4-fluorobenzyl bromide) followed by Li2CuCl4 (5 ml) solution keeping the temperature under 40° C. using a cool water bath. The mixture was stirred at room temperature for 2 h. To the mixture was added sat. NH4Cl solution (100 ml), the mixture was stirred for 30 min., the organic layer was separated and washed with 10% sodium thiosulfate solution (50 ml), followed by distilled water (100 ml). The organic layer was then dried over MgSO4 and concentrated to give 19 g of 2-(4-fluorobenzyl)thiophene as an oil. Purification was achieved by vacuum distillation (110° C., 5 mm Hg). The mixture was heated to reflux under nitrogen dropwise keeping reflux After the addition the mixture was heated under reflux for 2 h. under 40° C. the mixture was stirred for 30 min. the organic layer was separated washed with 10% sodium thiosulfate solution (50 ml) by distilled water (100 ml) The organic layer was then dried over MgSO4 concentrated

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

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

Procedure: To a suspension of Mg (3 g, 0.123 mol) in THF (40 ml) was added a small amount of solid I2 (20 mg). The mixture was heated to reflux under nitrogen. To the mixture was then added the 2-bromothiophene solution (5 ml) (19.6 g of 2-bromothiophene in 40 ml of THF). After the iodine color disappeared, to the suspension was added the rest of 2-bromothiophene solution dropwise keeping reflux. After the addition, the mixture was heated under reflux for 2 h., then was cooled to room temperature. To this mixture was added 4-fluorobenzyl iodide (or 4-fluorobenzyl bromide) followed by Li2CuCl4 (5 ml) solution keeping the temperature under 40° C. using a cool water bath. The mixture was stirred at room temperature for 2 h. To the mixture was added sat. NH4Cl solution (100 ml), the mixture was stirred for 30 min., the organic layer was separated and washed with 10% sodium thiosulfate solution (50 ml), followed by distilled water (100 ml). The organic layer was then dried over MgSO4 and concentrated to give 19 g of 2-(4-fluorobenzyl)thiophene as an oil. Purification was achieved by vacuum distillation (110° C., 5 mm Hg). The mixture was heated to reflux under nitrogen dropwise keeping reflux After the addition the mixture was heated under reflux for 2 h. under 40° C. the mixture was stirred for 30 min. the organic layer was separated washed with 10% sodium thiosulfate solution (50 ml) by distilled water (100 ml) The organic layer was then dried over MgSO4 concentrated

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

Procedure: mp. 151° -153° C., by the reaction of 1-[2,4-dichloro-β-(2,4-dichlorobenzyloxy)phenethyl]-imidazole and p-fluorobenzyl iodide.