methyl 3-chloro-4-hydroxy-5-iodobenzoate

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

Procedure: Methyl 3-chloro-4-hydroxy-5-iodobenzoate (3.00 g) was dissolved in N,N-dimethylformamide (20 mL), and potassium carbonate (3.98 g) and dimethylsulfuric acid (1.82 mL) were added to the solution, and then the mixture was stirred at room temperature for 5 hours. The reaction solution was filtered and water was added, and then the reaction mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound (2.96 g) as a pale yellow crystal. The reaction solution was filtered water was added the reaction mixture was extracted with ethyl acetate The organic layer was washed with water and saturated brine dried over anhydrous sodium sulfate The solvent was distilled off under reduced pressure

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

Procedure: Methyl 3-chloro-4-hydroxybenzoate (12.31 g) was dissolved in dichloromethane (100 mL) and methanol (12 mL), and N-iodosuccinimide (15.59 g) and trifluoromethanesulfonic acid (2 mL) were added to the solution, and then the mixture was stirred at room temperature for 2 hours. The solvent was distilled off under reduced pressure and the obtained residue was'washed with water (100 mL) to obtain the title compound (20.52 g) as a colorless crystal. The solvent was distilled off under reduced pressure

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

Procedure: Methyl 3-chloro-4-hydroxy-5-iodobenzoate (3.00 g) was dissolved in N,N-dimethylformamide (20 mL), and potassium carbonate (3.98 g) and dimethylsulfuric acid (1.82 mL) were added to the solution, and then the mixture was stirred at room temperature for 5 hours. The reaction solution was filtered and water was added, and then the reaction mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound (2.96 g) as a pale yellow crystal. The reaction solution was filtered water was added the reaction mixture was extracted with ethyl acetate The organic layer was washed with water and saturated brine dried over anhydrous sodium sulfate The solvent was distilled off under reduced pressure

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

Procedure: Methyl 3-chloro-4-hydroxybenzoate (12.31 g) was dissolved in dichloromethane (100 mL) and methanol (12 mL), and N-iodosuccinimide (15.59 g) and trifluoromethanesulfonic acid (2 mL) were added to the solution, and then the mixture was stirred at room temperature for 2 hours. The solvent was distilled off under reduced pressure and the obtained residue was'washed with water (100 mL) to obtain the title compound (20.52 g) as a colorless crystal. The solvent was distilled off under reduced pressure

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

Procedure: Methyl 3-chloro-4-hydroxy-5-iodobenzoate (3.00 g) was dissolved in N,N-dimethylformamide (20 mL), and potassium carbonate (3.98 g) and dimethylsulfuric acid (1.82 mL) were added to the solution, and then the mixture was stirred at room temperature for 5 hours. The reaction solution was filtered and water was added, and then the reaction mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound (2.96 g) as a pale yellow crystal. The reaction solution was filtered water was added the reaction mixture was extracted with ethyl acetate The organic layer was washed with water and saturated brine dried over anhydrous sodium sulfate The solvent was distilled off under reduced pressure

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

Procedure: Methyl 3-chloro-4-hydroxybenzoate (12.31 g) was dissolved in dichloromethane (100 mL) and methanol (12 mL), and N-iodosuccinimide (15.59 g) and trifluoromethanesulfonic acid (2 mL) were added to the solution, and then the mixture was stirred at room temperature for 2 hours. The solvent was distilled off under reduced pressure and the obtained residue was'washed with water (100 mL) to obtain the title compound (20.52 g) as a colorless crystal. The solvent was distilled off under reduced pressure