2-fluoro-3-methoxybenzaldehyde

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

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

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

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

Procedure: Potassium carbonate (3.6 g, 26.0 mmol) and dimethyl-1-diazo-2-oxopropylphosphonate (2.4 mL, 15.6 mmol) were added sequentially to a solution of 2-fluoro-3-methoxybenzaldehyde (2.0 g, 13.0 mmol) in methanol (100 mL), and the reaction was allowed to stir at room temperature for 16 h. After concentrating the reaction mixture under reduced pressure, the crude material was purified by flash chromatography (40 g silica gel column, 0-40% gradient ethyl acetate in hexanes) to provide a clear colorless oil (1.8 g, 92%). MS (GCMS) m/z 150. 1H NMR (400 MHz, CHLOROFORM-d) δ3.31 (d, J=0.78 Hz, 1H) 3.90 (s, 3H) 6.93-7.11 (m, 3H). After concentrating the reaction mixture under reduced pressure the crude material was purified by flash chromatography (40 g silica gel column, 0-40% gradient ethyl acetate in hexanes)

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

Procedure: To a stirred solution of sodium hydrogen carbonate (2.73 g, 32.5 mmol) in water (50 mL) was added hydroxylamine hydrochloride (2.30 g, 33.2 mmol) in portions over 30 min. The resultant solution was added to a vigorously stirred suspension of 2-fluoro-3-methoxybenzaldehyde (5.00 g, 32.5 mmol) in ethanol (45 mL) and the reaction mixture stirred at RT for 16 hr. The resultant precipitate was removed by filtration and washed with water (3×100 mL) and then allowed to dry in air to afford 2-fluoro-3-methoxybenzaldehyde oxime (14) (4.69 g, 85%) as a white crystalline solid: m/z 170 (M+H)+ (ES+). The resultant precipitate was removed by filtration washed with water (3×100 mL) to dry in air

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

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

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-fluoro-3-methoxybenzaldehyde (2.00 g) in toluene (50 mL) was added ethyl (triphenylphosphoranylidene)acetate (4.50 g), and the mixture was stirred at 110° C. for 4 hr. The reaction mixture was concentrated, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (2.50 g) as a colorless oil. The reaction mixture was concentrated the residue was purified by silica gel column chromatography (ethyl acetate/hexane)

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

Procedure: To a stirred solution of sodium hydrogen carbonate (2.73 g, 32.5 mmol) in water (50 mL) was added hydroxylamine hydrochloride (2.30 g, 33.2 mmol) in portions over 30 min. The resultant solution was added to a vigorously stirred suspension of 2-fluoro-3-methoxybenzaldehyde (5.00 g, 32.5 mmol) in ethanol (45 mL) and the reaction mixture stirred at RT for 16 hr. The resultant precipitate was removed by filtration and washed with water (3×100 mL) and then allowed to dry in air to afford 2-fluoro-3-methoxybenzaldehyde oxime (14) (4.69 g, 85%) as a white crystalline solid: m/z 170 (M+H)+ (ES+). The resultant precipitate was removed by filtration washed with water (3×100 mL) to dry in air

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

Procedure: Potassium carbonate (3.6 g, 26.0 mmol) and dimethyl-1-diazo-2-oxopropylphosphonate (2.4 mL, 15.6 mmol) were added sequentially to a solution of 2-fluoro-3-methoxybenzaldehyde (2.0 g, 13.0 mmol) in methanol (100 mL), and the reaction was allowed to stir at room temperature for 16 h. After concentrating the reaction mixture under reduced pressure, the crude material was purified by flash chromatography (40 g silica gel column, 0-40% gradient ethyl acetate in hexanes) to provide a clear colorless oil (1.8 g, 92%). MS (GCMS) m/z 150. 1H NMR (400 MHz, CHLOROFORM-d) δ3.31 (d, J=0.78 Hz, 1H) 3.90 (s, 3H) 6.93-7.11 (m, 3H). After concentrating the reaction mixture under reduced pressure the crude material was purified by flash chromatography (40 g silica gel column, 0-40% gradient ethyl acetate in hexanes)

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

Procedure: To a stirred solution of sodium hydrogen carbonate (2.73 g, 32.5 mmol) in water (50 mL) was added hydroxylamine hydrochloride (2.30 g, 33.2 mmol) in portions over 30 min. The resultant solution was added to a vigorously stirred suspension of 2-fluoro-3-methoxybenzaldehyde (5.00 g, 32.5 mmol) in ethanol (45 mL) and the reaction mixture stirred at RT for 16 hr. The resultant precipitate was removed by filtration and washed with water (3×100 mL) and then allowed to dry in air to afford 2-fluoro-3-methoxybenzaldehyde oxime (14) (4.69 g, 85%) as a white crystalline solid: m/z 170 (M+H)+ (ES+). The resultant precipitate was removed by filtration washed with water (3×100 mL) to dry in air

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