methyl 5-bromo-1-benzofuran-2-carboxylate

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

Procedure: To a stirred solution of 5-bromo-2-hydroxybenzaldehyde (14a, 1.5 g, 7.46 mmol) in DMF (20 mL), was added methyl bromoacetate (8.21 mmol, 0.78 mL) and potassium carbonate (4.12 g, 29.84 mmol). The reaction mixture was heated at 80° and stirred for 15 hours, quenched with water (100 mL) and extracted with ethyl acetate (2×50 mL). The organic phase was dried with sodium sulfate, concentrated and the residue was purified by flash chromatography on silica gel, eluent hexanes-EtOAc (9:1). This afforded 244a as a white solid (650 mg, 35% yield). 1H NMR: (DMSO) δ 8.01-8.00 (m, 1H), 7.73-7.70 (m, 2H), 7.66-7.63 (m, 1H), 3.89 (s, 3H). The reaction mixture was heated at 80° quenched with water (100 mL) extracted with ethyl acetate (2×50 mL) The organic phase was dried with sodium sulfate concentrated the residue was purified by flash chromatography on silica gel, eluent hexanes-EtOAc (9:1)

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

Procedure: To a stirred solution of 5-bromo-2-hydroxybenzaldehyde (14a, 1.5 g, 7.46 mmol) in DMF (20 mL), was added methyl bromoacetate (8.21 mmol, 0.78 mL) and potassium carbonate (4.12 g, 29.84 mmol). The reaction mixture was heated at 80° and stirred for 15 hours, quenched with water (100 mL) and extracted with ethyl acetate (2×50 mL). The organic phase was dried with sodium sulfate, concentrated and the residue was purified by flash chromatography on silica gel, eluent hexanes-EtOAc (9:1). This afforded 244a as a white solid (650 mg, 35% yield). 1H NMR: (DMSO) δ 8.01-8.00 (m, 1H), 7.73-7.70 (m, 2H), 7.66-7.63 (m, 1H), 3.89 (s, 3H). The reaction mixture was heated at 80° quenched with water (100 mL) extracted with ethyl acetate (2×50 mL) The organic phase was dried with sodium sulfate concentrated the residue was purified by flash chromatography on silica gel, eluent hexanes-EtOAc (9:1)

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

Procedure: To a stirred solution of 5-bromo-2-hydroxybenzaldehyde (14a, 1.5 g, 7.46 mmol) in DMF (20 mL), was added methyl bromoacetate (8.21 mmol, 0.78 mL) and potassium carbonate (4.12 g, 29.84 mmol). The reaction mixture was heated at 80° and stirred for 15 hours, quenched with water (100 mL) and extracted with ethyl acetate (2×50 mL). The organic phase was dried with sodium sulfate, concentrated and the residue was purified by flash chromatography on silica gel, eluent hexanes-EtOAc (9:1). This afforded 244a as a white solid (650 mg, 35% yield). 1H NMR: (DMSO) δ 8.01-8.00 (m, 1H), 7.73-7.70 (m, 2H), 7.66-7.63 (m, 1H), 3.89 (s, 3H). The reaction mixture was heated at 80° quenched with water (100 mL) extracted with ethyl acetate (2×50 mL) The organic phase was dried with sodium sulfate concentrated the residue was purified by flash chromatography on silica gel, eluent hexanes-EtOAc (9:1)

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

Procedure: To a stirred solution of 5-bromo-2-hydroxybenzaldehyde (14a, 1.5 g, 7.46 mmol) in DMF (20 mL), was added methyl bromoacetate (8.21 mmol, 0.78 mL) and potassium carbonate (4.12 g, 29.84 mmol). The reaction mixture was heated at 80° and stirred for 15 hours, quenched with water (100 mL) and extracted with ethyl acetate (2×50 mL). The organic phase was dried with sodium sulfate, concentrated and the residue was purified by flash chromatography on silica gel, eluent hexanes-EtOAc (9:1). This afforded 244a as a white solid (650 mg, 35% yield). 1H NMR: (DMSO) δ 8.01-8.00 (m, 1H), 7.73-7.70 (m, 2H), 7.66-7.63 (m, 1H), 3.89 (s, 3H). The reaction mixture was heated at 80° quenched with water (100 mL) extracted with ethyl acetate (2×50 mL) The organic phase was dried with sodium sulfate concentrated the residue was purified by flash chromatography on silica gel, eluent hexanes-EtOAc (9:1)