3-chloro-5-methoxybenzenethiol

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

Procedure: A mixture of 3-chloro-5-methoxybenzenethiol (1.90 g), methyl 4-bromo-3-oxopentanoate (2.50 g) and K2CO3 (1.80 g) in DMF (dry) (36.3 mL) was stirred at room temperature overnight. The reaction was quenched with H2O and diluted with EtOAc. The organic layer was separated, 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 (2.09 g). The reaction was quenched with H2O diluted with EtOAc The organic layer was separated 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:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of 3-chloro-5-methoxybenzenethiol (2.1 g) and DMF (dry) (30 mL) were added methyl 4-chloroacetoacetate (1.407 mL) and K2CO3 (1.994 g) at 0° C., and the mixture was stirred at room temperature for 5 h. The mixture was poured into water at room temperature and extracted with EtOAc. The organic layer was separated, 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 (1.440 g). extracted with EtOAc The organic layer was separated 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:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 3-chloro-5-methoxybenzenethiol (1.90 g), methyl 4-bromo-3-oxopentanoate (2.50 g) and K2CO3 (1.80 g) in DMF (dry) (36.3 mL) was stirred at room temperature overnight. The reaction was quenched with H2O and diluted with EtOAc. The organic layer was separated, 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 (2.09 g). The reaction was quenched with H2O diluted with EtOAc The organic layer was separated 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:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of 3-chloro-5-methoxybenzenethiol (2.1 g) and DMF (dry) (30 mL) were added methyl 4-chloroacetoacetate (1.407 mL) and K2CO3 (1.994 g) at 0° C., and the mixture was stirred at room temperature for 5 h. The mixture was poured into water at room temperature and extracted with EtOAc. The organic layer was separated, 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 (1.440 g). extracted with EtOAc The organic layer was separated washed successively with water and brine dried over MgSO4 concentrated in vacuo The residue was purified by silica gel column chromatography (EtOAc/hexane)