methyl 4-iodo-2-phenylmethoxybenzoate

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

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

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

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

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: 1H-Imidazole (0.044 g), D-proline (0.013 g), potassium carbonate (0.15 g), and copper(I) iodide (0.010 g) were added to a dimethyl sulfoxide (1 mL) solution of methyl 2-(benzyloxy)-4-iodobenzoate (0.20 g), followed by stirring under a nitrogen atmosphere at 90° C. for 1 hour. The reaction mixture was cooled to room temperature, and then dimethyl sulfoxide (0.5 mL), D-proline (0.013 g), and copper(I) iodide (0.010 g) were added thereto, followed by stirring under a nitrogen atmosphere at 90° C. for 2 hours. After cooling the reaction mixture to room temperature, water and ethyl acetate were added thereto, and the insoluble substance was removed by filtration. The organic layer was separated, washed with water and a saturated aqueous solution of sodium chloride sequentially, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [Fuji Silysia Chemical Ltd., PSQ100B (spherical), eluent: 90-20% hexane/ethyl acetate] to obtain 0.13 g of methyl 2-(benzyloxy)-4-(1H-imidazol-1-yl)benzoate as a white solid. The reaction mixture was cooled to room temperature by stirring under a nitrogen atmosphere at 90° C. for 2 hours After cooling the reaction mixture to room temperature the insoluble substance was removed by filtration The organic layer was separated washed with water a saturated aqueous solution of sodium chloride sequentially, and dried over anhydrous magnesium sulfate the solvent was evaporated under reduced pressure The obtained residue was purified by silica gel column chromatography [Fuji Silysia Chemical Ltd., PSQ100B (spherical), eluent: 90-20% hexane/ethyl acetate]

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

Procedure: 1H-Pyrazole (0.044 g), D-proline (0.013 g), potassium carbonate (0.15 g), and copper(I) iodide (0.010 g) were added to a dimethyl sulfoxide (1.5 mL) solution of methyl 2-(benzyloxy)-4-iodobenzoate (0.20 g), followed by stirring under a nitrogen atmosphere at 90° C. for 2 hours. The reaction mixture was cooled to room temperature, and then D-proline (0.013 g) and copper(I) iodide (0.010 g) were added thereto, followed by stirring under a nitrogen atmosphere at 100° C. for 2 hours. After cooling the reaction mixture to room temperature, water and ethyl acetate were added thereto, and the insoluble substance was removed by filtration. The organic layer was separated, washed with water and a saturated aqueous solution of sodium chloride sequentially, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [Fuji Silysia Chemical Ltd., PSQ100B (spherical), eluent: 100-60% hexane/ethyl acetate] to obtain 0.12 g of methyl 2-(benzyloxy)-4-(1H-pyrazol-1-yl)benzoate as a white solid. The reaction mixture was cooled to room temperature by stirring under a nitrogen atmosphere at 100° C. for 2 hours After cooling the reaction mixture to room temperature the insoluble substance was removed by filtration The organic layer was separated washed with water a saturated aqueous solution of sodium chloride sequentially, and dried over anhydrous magnesium sulfate the solvent was evaporated under reduced pressure The obtained residue was purified by silica gel column chromatography [Fuji Silysia Chemical Ltd., PSQ100B (spherical), eluent: 100-60% hexane/ethyl acetate]

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

Procedure: A 2.0 mol/L aqueous solution of sodium hydroxide (4.1 mL) was added to a solution mixture of methyl 2-(benzyloxy)-4-iodobenzoate (1.0 g) in dioxane (5.0 mL) and methanol (5.0 mL), followed by stirring at room temperature for 2 hours. The solvent was evaporated under reduced pressure, and water was added to the residue. After adjusting the pH to 2.5 with 6.0 mol/L hydrochloric acid under ice-cooling, ethyl acetate was added. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. Hexane and diisopropyl ether were added to the obtained residue, and the resulting solid substance was collected by filtration to obtain 0.93 g of 2-(benzyloxy)-4-iodobenzoic acid as a white solid. The solvent was evaporated under reduced pressure, and water was added to the residue cooling ethyl acetate was added The organic layer was separated washed with a saturated aqueous solution of sodium chloride dried over anhydrous magnesium sulfate the solvent was evaporated under reduced pressure Hexane and diisopropyl ether were added to the obtained residue the resulting solid substance was collected by filtration

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Potassium carbonate (1.9 g) and benzyl bromide (1.2 mL) were sequentially added to an N,N-dimethylacetamide (20 mL) solution of methyl 2-hydroxy-4-iodobenzoate (2.5 g), followed by stirring at 80° C. for 1 hour. The reaction mixture was cooled to room temperature, and then 1 mol/L hydrochloric acid and ethyl acetate were added thereto. The organic layer was separated, washed with 1 mol/L hydrochloric acid and a saturated aqueous solution of sodium chloride sequentially, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [Fuji Silysia Chemical Ltd., PSQ100B (spherical), eluent: 90-80% hexane/ethyl acetate] to obtain 3.3 g of methyl 2-(benzyloxy)-4-iodobenzoate as a yellow oily substance. The reaction mixture was cooled to room temperature The organic layer was separated washed with 1 mol/L hydrochloric acid a saturated aqueous solution of sodium chloride sequentially, and dried over anhydrous magnesium sulfate the solvent was evaporated under reduced pressure The obtained residue was purified by silica gel column chromatography [Fuji Silysia Chemical Ltd., PSQ100B (spherical), eluent: 90-80% hexane/ethyl acetate]

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

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