(3-fluoro-5-methoxyphenyl)methanol

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

Procedure: To a solution of (3-fluoro-5-methoxyphenyl)methanol (4.9 g, 30 mmol) in CCl4 (50 mL), PCl5 (13 g, 60 mmol) was added. The mixture was stirred at room temperature for 1 h. To this mixture, saturated Na2CO3 solution was slowly added until pH was adjusted to 7˜8. The mixture was extracted with DCM (3×15 mL), and the organic phase was concentrated to give a colorless oil, which was purified by silica-gel column chromatography (100% petroleum ether) to give 2.9 g of 1-(chloromethyl)-3-fluoro-5-methoxybenzene. 1H NMR (CDCl3): δ 6.68-6.72 (m, 2H), 6.54-6.59 (m, 1H), 4.51 (s, 2H), 3.81 (s, 3H). The mixture was extracted with DCM (3×15 mL) the organic phase was concentrated to give a colorless oil, which was purified by silica-gel column chromatography (100% petroleum ether)

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

Procedure: To a solution of 3-fluoro-5-methoxybenzoic acid (5.1 g, 30 mmol) in dry ether at 0° C., LiAlH4 (3.44 g, 90 mmol) was added slowly. The reaction mixture was stirred at room temperature for 3 h, and quenched by slow addition of 1 M aqueous HCl solution (30 mL). The mixture was extracted with ethyl acetate (3×15 mL). The organic phase was dried over Na2SO4 and concentrated to give 4.9 g of (3-fluoro-5-methoxyphenyl)methanol. 1H NMR (CDCl3): δ 6.67-6.70 (m, 2H), 6.50-6.55 (m, 1H), 4.64 (d, 2H), 3.79 (s, 3H). quenched by slow addition of 1 M aqueous HCl solution (30 mL) The mixture was extracted with ethyl acetate (3×15 mL) The organic phase was dried over Na2SO4 concentrated

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

Procedure: To a solution of (3-fluoro-5-methoxyphenyl)methanol (4.9 g, 30 mmol) in CCl4 (50 mL), PCl5 (13 g, 60 mmol) was added. The mixture was stirred at room temperature for 1 h. To this mixture, saturated Na2CO3 solution was slowly added until pH was adjusted to 7˜8. The mixture was extracted with DCM (3×15 mL), and the organic phase was concentrated to give a colorless oil, which was purified by silica-gel column chromatography (100% petroleum ether) to give 2.9 g of 1-(chloromethyl)-3-fluoro-5-methoxybenzene. 1H NMR (CDCl3): δ 6.68-6.72 (m, 2H), 6.54-6.59 (m, 1H), 4.51 (s, 2H), 3.81 (s, 3H). The mixture was extracted with DCM (3×15 mL) the organic phase was concentrated to give a colorless oil, which was purified by silica-gel column chromatography (100% petroleum ether)

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

Procedure: To a solution of 3-fluoro-5-methoxybenzoic acid (5.1 g, 30 mmol) in dry ether at 0° C., LiAlH4 (3.44 g, 90 mmol) was added slowly. The reaction mixture was stirred at room temperature for 3 h, and quenched by slow addition of 1 M aqueous HCl solution (30 mL). The mixture was extracted with ethyl acetate (3×15 mL). The organic phase was dried over Na2SO4 and concentrated to give 4.9 g of (3-fluoro-5-methoxyphenyl)methanol. 1H NMR (CDCl3): δ 6.67-6.70 (m, 2H), 6.50-6.55 (m, 1H), 4.64 (d, 2H), 3.79 (s, 3H). quenched by slow addition of 1 M aqueous HCl solution (30 mL) The mixture was extracted with ethyl acetate (3×15 mL) The organic phase was dried over Na2SO4 concentrated

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

Procedure: To a solution of (3-fluoro-5-methoxyphenyl)methanol (4.9 g, 30 mmol) in CCl4 (50 mL), PCl5 (13 g, 60 mmol) was added. The mixture was stirred at room temperature for 1 h. To this mixture, saturated Na2CO3 solution was slowly added until pH was adjusted to 7˜8. The mixture was extracted with DCM (3×15 mL), and the organic phase was concentrated to give a colorless oil, which was purified by silica-gel column chromatography (100% petroleum ether) to give 2.9 g of 1-(chloromethyl)-3-fluoro-5-methoxybenzene. 1H NMR (CDCl3): δ 6.68-6.72 (m, 2H), 6.54-6.59 (m, 1H), 4.51 (s, 2H), 3.81 (s, 3H). The mixture was extracted with DCM (3×15 mL) the organic phase was concentrated to give a colorless oil, which was purified by silica-gel column chromatography (100% petroleum ether)

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

Procedure: To a solution of 3-fluoro-5-methoxybenzoic acid (5.1 g, 30 mmol) in dry ether at 0° C., LiAlH4 (3.44 g, 90 mmol) was added slowly. The reaction mixture was stirred at room temperature for 3 h, and quenched by slow addition of 1 M aqueous HCl solution (30 mL). The mixture was extracted with ethyl acetate (3×15 mL). The organic phase was dried over Na2SO4 and concentrated to give 4.9 g of (3-fluoro-5-methoxyphenyl)methanol. 1H NMR (CDCl3): δ 6.67-6.70 (m, 2H), 6.50-6.55 (m, 1H), 4.64 (d, 2H), 3.79 (s, 3H). quenched by slow addition of 1 M aqueous HCl solution (30 mL) The mixture was extracted with ethyl acetate (3×15 mL) The organic phase was dried over Na2SO4 concentrated