660842-05-7

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

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

Procedure: In a nitrogen stream, an n-butyllithium hexane solution (2.44 M, 2.4 mL) was added dropwise to a solution of 1-benzyloxy-2-bromo-4-fluorobenzene (1.5 g, 5.33 mmol) in THF (60 mL) at −78° C. and the mixture was stirred at the same temperature for 30 minutes. To this solution, a solution of 4-methoxybenzaldehyde (0.6 g, 4.42 mmol) in THF (20 mL) was added dropwise at −78° C. The reaction mixture was stirred at the same temperature for one hour, and then a saturated ammonium chloride aqueous solution was added thereto and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution and dried (anhydrous magnesium sulfate), and then the solvent was distilled under reduced pressure. The obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:5)] to obtain the title compound (0.98 g, 66%). The reaction mixture was stirred at the same temperature for one hour the mixture was extracted with ethyl acetate The organic layer was washed with a saturated sodium chloride aqueous solution dried (anhydrous magnesium sulfate) the solvent was distilled under reduced pressure The obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:5)]

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

Procedure: In a nitrogen stream, an n-butyllithium hexane solution (2.44 M, 2.4 mL) was added dropwise to a solution of 1-benzyloxy-2-bromo-4-fluorobenzene (1.5 g, 5.33 mmol) in THF (60 mL) at −78° C. and the mixture was stirred at the same temperature for 30 minutes. To this solution, a solution of 4-methoxybenzaldehyde (0.6 g, 4.42 mmol) in THF (20 mL) was added dropwise at −78° C. The reaction mixture was stirred at the same temperature for one hour, and then a saturated ammonium chloride aqueous solution was added thereto and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution and dried (anhydrous magnesium sulfate), and then the solvent was distilled under reduced pressure. The obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:5)] to obtain the title compound (0.98 g, 66%). The reaction mixture was stirred at the same temperature for one hour the mixture was extracted with ethyl acetate The organic layer was washed with a saturated sodium chloride aqueous solution dried (anhydrous magnesium sulfate) the solvent was distilled under reduced pressure The obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:5)]

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

Procedure: To a mixture of 2-bromo-4-fluorophenol (24.7 g, 129 mmol), tetrabutylammonium iodide (4.8 g, 13.0 mmol), potassium carbonate (35.9 g, 260 mmol) and N,N-dimethylformamide (390 mL), benzyl bromide (23.5 g, 137 mmol) was added at room temperature and stirred for 1.5 hours. The reaction mixture was poured into a mixture of ethyl acetate and saturated aqueous sodium chloride, and then extracted with ethyl acetate. The organic phase was washed twice with saturated aqueous sodium chloride and then dried over anhydrous magnesium sulfate. After the solvent was distilled off under reduced pressure, the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=90:10-80:20) to give 1-benzyloxy-2-bromo-4-fluoro-benzene (33.0 g, 90%). was added at room temperature extracted with ethyl acetate The organic phase was washed twice with saturated aqueous sodium chloride dried over anhydrous magnesium sulfate After the solvent was distilled off under reduced pressure the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=90:10-80:20)

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

Procedure: To a mixture of 2-bromo-4-fluorophenol (24.7 g, 129 mmol), tetrabutylammonium iodide (4.8 g, 13.0 mmol), potassium carbonate (35.9 g, 260 mmol) and N,N-dimethylformamide (390 mL), benzyl bromide (23.5 g, 137 mmol) was added at room temperature and stirred for 1.5 hours. The reaction mixture was poured into a mixture of ethyl acetate and saturated aqueous sodium chloride, and then extracted with ethyl acetate. The organic phase was washed twice with saturated aqueous sodium chloride and then dried over anhydrous magnesium sulfate. After the solvent was distilled off under reduced pressure, the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=90:10–80:20) to give 1-benzyloxy-2-bromo-4-fluorobenzene (33.0 g, 90%). was added at room temperature extracted with ethyl acetate The organic phase was washed twice with saturated aqueous sodium chloride dried over anhydrous magnesium sulfate After the solvent was distilled off under reduced pressure the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=90:10–80:20)

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

Procedure: In a nitrogen stream, an n-butyllithium hexane solution (2.44 M, 2.4 mL) was added dropwise to a solution of 1-benzyloxy-2-bromo-4-fluorobenzene (1.5 g, 5.33 mmol) in THF (60 mL) at −78° C. and the mixture was stirred at the same temperature for 30 minutes. To this solution, a solution of 4-methoxybenzaldehyde (0.6 g, 4.42 mmol) in THF (20 mL) was added dropwise at −78° C. The reaction mixture was stirred at the same temperature for one hour, and then a saturated ammonium chloride aqueous solution was added thereto and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution and dried (anhydrous magnesium sulfate), and then the solvent was distilled under reduced pressure. The obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:5)] to obtain the title compound (0.98 g, 66%). The reaction mixture was stirred at the same temperature for one hour the mixture was extracted with ethyl acetate The organic layer was washed with a saturated sodium chloride aqueous solution dried (anhydrous magnesium sulfate) the solvent was distilled under reduced pressure The obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:5)]