5-chloro-2-fluoro-3-methoxybenzenethiol

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

Procedure: To a mixture of 5-chloro-2-fluoro-3-methoxybenzenethiol (303 mg) and DMF (dry) (12 mL) were added K2CO3 (239 mg) and methyl 4-chloro-3-oxobutanoate (0.204 mL) at 0° C. The mixture was stirred at room temperature for 45 min. The mixture was diluted with water and extracted with EtOAc. The combined organic layer was washed successively with water and brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (402 mg). extracted with EtOAc The combined organic layer was washed successively with water and brine dried over MgSO4 concentrated in vacuo The residue was purified by silica gel column chromatography (EtOAc/hexane)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of 5-chloro-2-fluoro-1-methoxy-3-(methylsulfinyl)benzene (501 mg) and CH3CN (20 mL) was added TFAA (0.953 mL) at 0° C. The mixture was stirred at 0° C. for 1 h and then at room temperature for 1 h. The mixture was concentrated. The residue was dissolved in a mixture of MeOH (3.5 mL) and TEA (3.5 mL) at 0° C. The solution was stirred at 0° C. for 10 min, and concentrated in vacuo. The mixture was diluted with saturated aqueous NH4Cl and extracted with EtOAc. The organic layer was extracted with 1N NaOH. The aqueous layer was acidified with 1N HCl and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo to give the title compound (303 mg). at room temperature for 1 h The mixture was concentrated The residue was dissolved in a mixture of MeOH (3.5 mL) and TEA (3.5 mL) at 0° C The solution was stirred at 0° C. for 10 min concentrated in vacuo The mixture was diluted with saturated aqueous NH4Cl extracted with EtOAc The organic layer was extracted with 1N NaOH extracted with EtOAc The organic layer was washed with brine dried over MgSO4 concentrated in vacuo

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of 5-chloro-2-fluoro-1-methoxy-3-(methylsulfinyl)benzene (501 mg) and CH3CN (20 mL) was added TFAA (0.953 mL) at 0° C. The mixture was stirred at 0° C. for 1 h and then at room temperature for 1 h. The mixture was concentrated. The residue was dissolved in a mixture of MeOH (3.5 mL) and TEA (3.5 mL) at 0° C. The solution was stirred at 0° C. for 10 min, and concentrated in vacuo. The mixture was diluted with saturated aqueous NH4Cl and extracted with EtOAc. The organic layer was extracted with 1N NaOH. The aqueous layer was acidified with 1N HCl and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo to give the title compound (303 mg). at room temperature for 1 h The mixture was concentrated The residue was dissolved in a mixture of MeOH (3.5 mL) and TEA (3.5 mL) at 0° C The solution was stirred at 0° C. for 10 min concentrated in vacuo The mixture was diluted with saturated aqueous NH4Cl extracted with EtOAc The organic layer was extracted with 1N NaOH extracted with EtOAc The organic layer was washed with brine dried over MgSO4 concentrated in vacuo

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

Procedure: To a mixture of 5-chloro-2-fluoro-3-methoxybenzenethiol (303 mg) and DMF (dry) (12 mL) were added K2CO3 (239 mg) and methyl 4-chloro-3-oxobutanoate (0.204 mL) at 0° C. The mixture was stirred at room temperature for 45 min. The mixture was diluted with water and extracted with EtOAc. The combined organic layer was washed successively with water and brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (402 mg). extracted with EtOAc The combined organic layer was washed successively with water and brine dried over MgSO4 concentrated in vacuo The residue was purified by silica gel column chromatography (EtOAc/hexane)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of 5-chloro-2-fluoro-1-methoxy-3-(methylsulfinyl)benzene (501 mg) and CH3CN (20 mL) was added TFAA (0.953 mL) at 0° C. The mixture was stirred at 0° C. for 1 h and then at room temperature for 1 h. The mixture was concentrated. The residue was dissolved in a mixture of MeOH (3.5 mL) and TEA (3.5 mL) at 0° C. The solution was stirred at 0° C. for 10 min, and concentrated in vacuo. The mixture was diluted with saturated aqueous NH4Cl and extracted with EtOAc. The organic layer was extracted with 1N NaOH. The aqueous layer was acidified with 1N HCl and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo to give the title compound (303 mg). at room temperature for 1 h The mixture was concentrated The residue was dissolved in a mixture of MeOH (3.5 mL) and TEA (3.5 mL) at 0° C The solution was stirred at 0° C. for 10 min concentrated in vacuo The mixture was diluted with saturated aqueous NH4Cl extracted with EtOAc The organic layer was extracted with 1N NaOH extracted with EtOAc The organic layer was washed with brine dried over MgSO4 concentrated in vacuo