2-chloro-4-fluoro-1-(2-methoxyethoxy)benzene

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To 2-chloro-4-fluoro-1-(2-methoxy-ethoxy)-benzene (122, 1.50 g, 7.33 mmol) in tetrahydrofuran (44.0 mL), under an atmosphere of nitrogen at −78° C., n-butyllithium (2.50 M in hexane, 3.08 mL) was added slowly. After 15 minutes, N,N-dimethylformamide (0.681 mL, 8.80 mmol) was added to the reaction. After 30 minutes, the reaction was allowed to warm to room temperature. The reaction was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 30% ethyl acetate in hexane to give a light yellow solid (123, 1.20 g, 70.4%). After 30 minutes extracted with ethyl acetate The organic layer was dried over anhydrous sodium sulfate filtered The filtrate was concentrated purified by silica gel column chromatography eluting with 30% ethyl acetate in hexane to give a light yellow solid (123, 1.20 g, 70.4%)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To 2-chloro-4-fluoro-1-(2-methoxy-ethoxy)-benzene (122, 1.50 g, 7.33 mmol) in tetrahydrofuran (44.0 mL), under an atmosphere of nitrogen at −78° C., n-butyllithium (2.50 M in hexane, 3.08 mL) was added slowly. After 15 minutes, N,N-dimethylformamide (0.681 mL, 8.80 mmol) was added to the reaction. After 30 minutes, the reaction was allowed to warm to room temperature. The reaction was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 30% ethyl acetate in hexane to give a light yellow solid (123, 1.20 g, 70.4%). After 30 minutes extracted with ethyl acetate The organic layer was dried over anhydrous sodium sulfate filtered The filtrate was concentrated purified by silica gel column chromatography eluting with 30% ethyl acetate in hexane to give a light yellow solid (123, 1.20 g, 70.4%)

反応条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To 2-chloro-4-fluorophenol (52, 2.40 mL, 0.0213 mol) in N,N-dimethylformamide (30.0 mL), 1-bromo-2-methoxy-ethane (2.00 mL, 0.0213 mol) and potassium carbonate (3.00 g, 0.0217 mol) were added under an atmosphere of nitrogen. The reaction was stirred at 80° C. for 2 hours. The reaction was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 20% ethyl acetate in hexane to give a colorless oil (122, 1.50 g, 34.4%). extracted with ethyl acetate The organic layer was dried over anhydrous sodium sulfate filtered The filtrate was concentrated purified by silica gel column chromatography eluting with 20% ethyl acetate in hexane to give a colorless oil (122, 1.50 g, 34.4%)

反応条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To 2-chloro-4-fluorophenol (52, 2.40 mL, 0.0213 mol) in N,N-dimethylformamide (30.0 mL), 1-bromo-2-methoxy-ethane (2.00 mL, 0.0213 mol) and potassium carbonate (3.00 g, 0.0217 mol) were added under an atmosphere of nitrogen. The reaction was stirred at 80° C. for 2 hours. The reaction was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 20% ethyl acetate in hexane to give a colorless oil (122, 1.50 g, 34.4%). extracted with ethyl acetate The organic layer was dried over anhydrous sodium sulfate filtered The filtrate was concentrated purified by silica gel column chromatography eluting with 20% ethyl acetate in hexane to give a colorless oil (122, 1.50 g, 34.4%)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To 2-chloro-4-fluoro-1-(2-methoxy-ethoxy)-benzene (122, 1.50 g, 7.33 mmol) in tetrahydrofuran (44.0 mL), under an atmosphere of nitrogen at −78° C., n-butyllithium (2.50 M in hexane, 3.08 mL) was added slowly. After 15 minutes, N,N-dimethylformamide (0.681 mL, 8.80 mmol) was added to the reaction. After 30 minutes, the reaction was allowed to warm to room temperature. The reaction was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 30% ethyl acetate in hexane to give a light yellow solid (123, 1.20 g, 70.4%). After 30 minutes extracted with ethyl acetate The organic layer was dried over anhydrous sodium sulfate filtered The filtrate was concentrated purified by silica gel column chromatography eluting with 30% ethyl acetate in hexane to give a light yellow solid (123, 1.20 g, 70.4%)

反応条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To 2-chloro-4-fluorophenol (52, 2.40 mL, 0.0213 mol) in N,N-dimethylformamide (30.0 mL), 1-bromo-2-methoxy-ethane (2.00 mL, 0.0213 mol) and potassium carbonate (3.00 g, 0.0217 mol) were added under an atmosphere of nitrogen. The reaction was stirred at 80° C. for 2 hours. The reaction was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 20% ethyl acetate in hexane to give a colorless oil (122, 1.50 g, 34.4%). extracted with ethyl acetate The organic layer was dried over anhydrous sodium sulfate filtered The filtrate was concentrated purified by silica gel column chromatography eluting with 20% ethyl acetate in hexane to give a colorless oil (122, 1.50 g, 34.4%)

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To 2-chloro-4-fluoro-1-(2-methoxy-ethoxy)-benzene (122, 1.50 g, 7.33 mmol) in tetrahydrofuran (44.0 mL), under an atmosphere of nitrogen at −78° C., n-butyllithium (2.50 M in hexane, 3.08 mL) was added slowly. After 15 minutes, N,N-dimethylformamide (0.681 mL, 8.80 mmol) was added to the reaction. After 30 minutes, the reaction was allowed to warm to room temperature. The reaction was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 30% ethyl acetate in hexane to give a light yellow solid (123, 1.20 g, 70.4%). After 30 minutes extracted with ethyl acetate The organic layer was dried over anhydrous sodium sulfate filtered The filtrate was concentrated purified by silica gel column chromatography eluting with 30% ethyl acetate in hexane to give a light yellow solid (123, 1.20 g, 70.4%)

反応条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To 2-chloro-4-fluorophenol (52, 2.40 mL, 0.0213 mol) in N,N-dimethylformamide (30.0 mL), 1-bromo-2-methoxy-ethane (2.00 mL, 0.0213 mol) and potassium carbonate (3.00 g, 0.0217 mol) were added under an atmosphere of nitrogen. The reaction was stirred at 80° C. for 2 hours. The reaction was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 20% ethyl acetate in hexane to give a colorless oil (122, 1.50 g, 34.4%). extracted with ethyl acetate The organic layer was dried over anhydrous sodium sulfate filtered The filtrate was concentrated purified by silica gel column chromatography eluting with 20% ethyl acetate in hexane to give a colorless oil (122, 1.50 g, 34.4%)