2-CHLORO-4,5-DIFLUOROBENZALDEHYDE

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

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

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 2-chloro-4,5-difluoro-benzaldehyde (110, 0.40 g, 2.30 mmol, prepared as described in Example 37) in N,N-dimethylformamide (10.0 mL) were added 2-(2-methoxyethoxy)-ethanol, (0.327 g, 2.72 mmol) and cesium carbonate (0.886 g, 2.72 mmol). The reaction was stirred at 90° C. overnight. The reaction was poured into water, acidified to pH around 5, 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 white solid (111, 0.24 g, 61.0%). MS (ESI) [M+H+]+=173.1. 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 white solid (111, 0.24 g, 61.0%)

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 2-chloro-4,5-difluoro-benzaldehyde (110, 0.40 g, 2.30 mmol, prepared as described in Example 37) in N,N-dimethylformamide (10.0 mL) were added 2-(2-methoxyethoxy)-ethanol, (0.327 g, 2.72 mmol) and cesium carbonate (0.886 g, 2.72 mmol). The reaction was stirred at 90° C. overnight. The reaction was poured into water, acidified to pH around 5, 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 white solid (111, 0.24 g, 61.0%). MS (ESI) [M+H+]+=173.1. 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 white solid (111, 0.24 g, 61.0%)

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 2-chloro-4,5-difluoro-benzaldehyde (110, 0.40 g, 0.0023 mol) in N,N-dimethylformamide (10.0 mL), 2-(2-methoxyethoxy)-ethanol (0.327 g, 2.72 mmol) and cesium carbonate (0.886 g, 2.72 mmol) were added. The reaction was stirred at 90° C. overnight. The reaction was poured into water, acidified to pH around 5, and extracted with ethyl acetate. The organic layer was dried over an hydrous 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 white solid (121, 0.15 g, 24.0%). extracted with ethyl acetate The organic layer was dried over an hydrous sodium sulfate filtered The filtrate was concentrated purified by silica gel column chromatography eluting with 30% ethyl acetate in hexane to give a white solid (121, 0.15 g, 24.0%)

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 2-chloro-4,5-difluoro-benzaldehyde (110, 0.40 g, 0.0023 mol) in N,N-dimethylformamide (10.0 mL), 2-(2-methoxyethoxy)-ethanol (0.327 g, 2.72 mmol) and cesium carbonate (0.886 g, 2.72 mmol) were added. The reaction was stirred at 90° C. overnight. The reaction was poured into water, acidified to pH around 5, and extracted with ethyl acetate. The organic layer was dried over an hydrous 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 white solid (121, 0.15 g, 24.0%). extracted with ethyl acetate The organic layer was dried over an hydrous sodium sulfate filtered The filtrate was concentrated purified by silica gel column chromatography eluting with 30% ethyl acetate in hexane to give a white solid (121, 0.15 g, 24.0%)

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

Procedure: To (2-chloro-4,5-difluoro-phenyl)-methanol (120, 2.40 g, 0.0134 mol) in dichloromethane (40.0 mL) was added Dess-Martin periodinane (6.84 g, 0.0161 mol). The reaction was stirred at room temperature for 10 minutes. The reaction was poured into aqueous potassium carbonate 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 white solid (110, 1.7 g, 71.6%). 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 white solid (110, 1.7 g, 71.6%)

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

Procedure: To (2-chloro-4,5-difluoro-phenyl)-methanol (120, 2.40 g, 0.0134 mol) in dichloromethane (40.0 mL) was added Dess-Martin periodinane (6.84 g, 0.0161 mol). The reaction was stirred at room temperature for 10 minutes. The reaction was poured into aqueous potassium carbonate 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 white solid (110, 1.7 g, 71.6%). 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 white solid (110, 1.7 g, 71.6%)

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 2-chloro-4,5-difluoro-benzaldehyde (110, 0.40 g, 2.30 mmol, prepared as described in Example 37) in N,N-dimethylformamide (10.0 mL) were added 2-(2-methoxyethoxy)-ethanol, (0.327 g, 2.72 mmol) and cesium carbonate (0.886 g, 2.72 mmol). The reaction was stirred at 90° C. overnight. The reaction was poured into water, acidified to pH around 5, 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 white solid (111, 0.24 g, 61.0%). MS (ESI) [M+H+]+=173.1. 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 white solid (111, 0.24 g, 61.0%)

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 2-chloro-4,5-difluoro-benzaldehyde (110, 0.40 g, 0.0023 mol) in N,N-dimethylformamide (10.0 mL), 2-(2-methoxyethoxy)-ethanol (0.327 g, 2.72 mmol) and cesium carbonate (0.886 g, 2.72 mmol) were added. The reaction was stirred at 90° C. overnight. The reaction was poured into water, acidified to pH around 5, and extracted with ethyl acetate. The organic layer was dried over an hydrous 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 white solid (121, 0.15 g, 24.0%). extracted with ethyl acetate The organic layer was dried over an hydrous sodium sulfate filtered The filtrate was concentrated purified by silica gel column chromatography eluting with 30% ethyl acetate in hexane to give a white solid (121, 0.15 g, 24.0%)

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

Procedure: To (2-chloro-4,5-difluoro-phenyl)-methanol (120, 2.40 g, 0.0134 mol) in dichloromethane (40.0 mL) was added Dess-Martin periodinane (6.84 g, 0.0161 mol). The reaction was stirred at room temperature for 10 minutes. The reaction was poured into aqueous potassium carbonate 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 white solid (110, 1.7 g, 71.6%). 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 white solid (110, 1.7 g, 71.6%)

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