1-fluoro-4-(3-iodopropyl)benzene

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

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

Procedure: Subsequently, sodium acetylide (18% slurry in xylene) (50 ml) was added to hexamethylphosphoramide (20 ml) with stirring, and to the resulting mixture was furthermore added a solution of 3-(4-fluorophenyl)-1-iodopropane (7.00 g, 26.5 mmol) obtained above in dry dimethylformamide (20 ml) with stirring under ice-cooling, and then the resulting mixture was stirred at room temperature for 2 hours. After stirring, ice-cold water was added to the reaction mixture carefully with stirring under ice-cooling, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. After filtration, the solvent was removed in vacuo, and the residue was purified by flash chromatography on a silica gel column using hexane as the eluent to afford the title compound (2.67 g, yield: 62%) as a colorless oil. with stirring under ice- cooling the resulting mixture was stirred at room temperature for 2 hours After stirring ice-cold water was added to the reaction mixture carefully with stirring under ice- cooling the resulting mixture was extracted with ethyl acetate The organic layer was washed with saturated aqueous sodium chloride solution dried over anhydrous magnesium sulfate After filtration the solvent was removed in vacuo the residue was purified by flash chromatography on a silica gel column

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

Procedure: The title compound was prepared from 3-(4-fluorophenyl propyliodide and 1-benzyl-4-piperidone as described in Example 122.

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

Procedure: To a solution of 2.26 g (14.65 mmol) of 3-(4-fluorophenyl propanol and 3.6 mL (44 mmol) of pyridine in 40 mL of CH2Cl2 at 0° C. was added 5.1 g (29.3 mmol) of methanesulfonic anhydride and the reaction mixture was sitirred for 4 h at rt. The reaction mixture was partitioned between 100 mL of CH2Cl2 and 20 of sat'd NaHCO3 solution. The organic fraction was washed 3 times with sat'd NaHCO3 solution and sat'd NaCl solution, dried over MgSO4 and the filtrate was concentrated several times from heptane to remove pyridine. To the residue in 50 mL of acetone was added 6 g (44 mmol) of LiI and the reaction mixture was Stirred for 20 hr. The reaction mixture was poured into 200 mL of H2O and extracted with ether. The combined organic fractions were washed with sat'd NaCl solution, dried over MgSO4, filtered and the filtrate was concentrated. The residue was purified by chromatography (silica, hexanes: ethyl acetate, 9:1) to give 3.25 g of the title compound. The reaction mixture was partitioned between 100 mL of CH2Cl2 and 20 of sat'd NaHCO3 solution The organic fraction was washed 3 times with sat'd NaHCO3 solution dried over MgSO4 the filtrate was concentrated several times from heptane to remove pyridine extracted with ether The combined organic fractions were washed with sat'd NaCl solution dried over MgSO4 filtered the filtrate was concentrated The residue was purified by chromatography (silica, hexanes: ethyl acetate, 9:1)

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

Procedure: Subsequently, sodium acetylide (18% slurry in xylene) (50 ml) was added to hexamethylphosphoramide (20 ml) with stirring, and to the resulting mixture was furthermore added a solution of 3-(4-fluorophenyl)-1-iodopropane (7.00 g, 26.5 mmol) obtained above in dry dimethylformamide (20 ml) with stirring under ice-cooling, and then the resulting mixture was stirred at room temperature for 2 hours. After stirring, ice-cold water was added to the reaction mixture carefully with stirring under ice-cooling, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. After filtration, the solvent was removed in vacuo, and the residue was purified by flash chromatography on a silica gel column using hexane as the eluent to afford the title compound (2.67 g, yield: 62%) as a colorless oil. with stirring under ice- cooling the resulting mixture was stirred at room temperature for 2 hours After stirring ice-cold water was added to the reaction mixture carefully with stirring under ice- cooling the resulting mixture was extracted with ethyl acetate The organic layer was washed with saturated aqueous sodium chloride solution dried over anhydrous magnesium sulfate After filtration the solvent was removed in vacuo the residue was purified by flash chromatography on a silica gel column

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

Procedure: Subsequently, sodium acetylide (18% slurry in xylene) (50 ml) was added to hexamethylphosphoramide (20 ml) with stirring, and to the resulting mixture was furthermore added a solution of 3-(4-fluorophenyl)-1-iodopropane (7.00 g, 26.5 mmol) obtained above in dry dimethylformamide (20 ml) with stirring under ice-cooling, and then the resulting mixture was stirred at room temperature for 2 hours. After stirring, ice-cold water was added to the reaction mixture carefully with stirring under ice-cooling, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. After filtration, the solvent was removed in vacuo, and the residue was purified by flash chromatography on a silica gel column using hexane as the eluent to afford the title compound (2.67 g, yield: 62%) as a colorless oil. with stirring under ice- cooling the resulting mixture was stirred at room temperature for 2 hours After stirring ice-cold water was added to the reaction mixture carefully with stirring under ice- cooling the resulting mixture was extracted with ethyl acetate The organic layer was washed with saturated aqueous sodium chloride solution dried over anhydrous magnesium sulfate After filtration the solvent was removed in vacuo the residue was purified by flash chromatography on a silica gel column

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

Procedure: Subsequently, sodium acetylide (18% slurry in xylene) (50 ml) was added to hexamethylphosphoramide (20 ml) with stirring, and to the resulting mixture was furthermore added a solution of 3-(4-fluorophenyl)-1-iodopropane (7.00 g, 26.5 mmol) obtained above in dry dimethylformamide (20 ml) with stirring under ice-cooling, and then the resulting mixture was stirred at room temperature for 2 hours. After stirring, ice-cold water was added to the reaction mixture carefully with stirring under ice-cooling, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. After filtration, the solvent was removed in vacuo, and the residue was purified by flash chromatography on a silica gel column using hexane as the eluent to afford the title compound (2.67 g, yield: 62%) as a colorless oil. with stirring under ice- cooling the resulting mixture was stirred at room temperature for 2 hours After stirring ice-cold water was added to the reaction mixture carefully with stirring under ice- cooling the resulting mixture was extracted with ethyl acetate The organic layer was washed with saturated aqueous sodium chloride solution dried over anhydrous magnesium sulfate After filtration the solvent was removed in vacuo the residue was purified by flash chromatography on a silica gel column

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

Procedure: The title compound was prepared from 3-(4-fluorophenyl propyliodide and 1-benzyl-4-piperidone as described in Example 122.

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

Procedure: To a solution of 2.26 g (14.65 mmol) of 3-(4-fluorophenyl propanol and 3.6 mL (44 mmol) of pyridine in 40 mL of CH2Cl2 at 0° C. was added 5.1 g (29.3 mmol) of methanesulfonic anhydride and the reaction mixture was sitirred for 4 h at rt. The reaction mixture was partitioned between 100 mL of CH2Cl2 and 20 of sat'd NaHCO3 solution. The organic fraction was washed 3 times with sat'd NaHCO3 solution and sat'd NaCl solution, dried over MgSO4 and the filtrate was concentrated several times from heptane to remove pyridine. To the residue in 50 mL of acetone was added 6 g (44 mmol) of LiI and the reaction mixture was Stirred for 20 hr. The reaction mixture was poured into 200 mL of H2O and extracted with ether. The combined organic fractions were washed with sat'd NaCl solution, dried over MgSO4, filtered and the filtrate was concentrated. The residue was purified by chromatography (silica, hexanes: ethyl acetate, 9:1) to give 3.25 g of the title compound. The reaction mixture was partitioned between 100 mL of CH2Cl2 and 20 of sat'd NaHCO3 solution The organic fraction was washed 3 times with sat'd NaHCO3 solution dried over MgSO4 the filtrate was concentrated several times from heptane to remove pyridine extracted with ether The combined organic fractions were washed with sat'd NaCl solution dried over MgSO4 filtered the filtrate was concentrated The residue was purified by chromatography (silica, hexanes: ethyl acetate, 9:1)

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

Procedure: To a solution of 2.26 g (14.65 mmol) of 3-(4-fluorophenyl propanol and 3.6 mL (44 mmol) of pyridine in 40 mL of CH2Cl2 at 0° C. was added 5.1 g (29.3 mmol) of methanesulfonic anhydride and the reaction mixture was sitirred for 4 h at rt. The reaction mixture was partitioned between 100 mL of CH2Cl2 and 20 of sat'd NaHCO3 solution. The organic fraction was washed 3 times with sat'd NaHCO3 solution and sat'd NaCl solution, dried over MgSO4 and the filtrate was concentrated several times from heptane to remove pyridine. To the residue in 50 mL of acetone was added 6 g (44 mmol) of LiI and the reaction mixture was Stirred for 20 hr. The reaction mixture was poured into 200 mL of H2O and extracted with ether. The combined organic fractions were washed with sat'd NaCl solution, dried over MgSO4, filtered and the filtrate was concentrated. The residue was purified by chromatography (silica, hexanes: ethyl acetate, 9:1) to give 3.25 g of the title compound. The reaction mixture was partitioned between 100 mL of CH2Cl2 and 20 of sat'd NaHCO3 solution The organic fraction was washed 3 times with sat'd NaHCO3 solution dried over MgSO4 the filtrate was concentrated several times from heptane to remove pyridine extracted with ether The combined organic fractions were washed with sat'd NaCl solution dried over MgSO4 filtered the filtrate was concentrated The residue was purified by chromatography (silica, hexanes: ethyl acetate, 9:1)

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

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

Procedure: Subsequently, sodium acetylide (18% slurry in xylene) (50 ml) was added to hexamethylphosphoramide (20 ml) with stirring, and to the resulting mixture was furthermore added a solution of 3-(4-fluorophenyl)-1-iodopropane (7.00 g, 26.5 mmol) obtained above in dry dimethylformamide (20 ml) with stirring under ice-cooling, and then the resulting mixture was stirred at room temperature for 2 hours. After stirring, ice-cold water was added to the reaction mixture carefully with stirring under ice-cooling, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. After filtration, the solvent was removed in vacuo, and the residue was purified by flash chromatography on a silica gel column using hexane as the eluent to afford the title compound (2.67 g, yield: 62%) as a colorless oil. with stirring under ice- cooling the resulting mixture was stirred at room temperature for 2 hours After stirring ice-cold water was added to the reaction mixture carefully with stirring under ice- cooling the resulting mixture was extracted with ethyl acetate The organic layer was washed with saturated aqueous sodium chloride solution dried over anhydrous magnesium sulfate After filtration the solvent was removed in vacuo the residue was purified by flash chromatography on a silica gel column