2-amino-3-bromo-5-chlorobenzaldehyde

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

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

Procedure: To a suspension of 2-amino-3-bromo-5-chlorobenzaldehyde (3.0 g, 12.8 mmol) in a water (4 mL) and hydrochloric acid (4 mL) mixture at 0° C. was added a solution of sodium nitrite (1.1 g, 16.0 mmol) in water (ca. 2 mL) dropwise. After 30 min, the ice bath was removed and the reaction stirred at room temperature for 30 min forming a white suspension. The solids were removed by filtration. The mother liquor was cooled to 0° C. and treated with sodium azide (0.8 g, 12.8 mmol) in water (2.0 mL). The ice bath was removed and stirring was continued for 30 min. The resulting solid was collected by filtration and dried in vacuo for several hours to afford 2.6 g (76%) as a white solid. 1H-NMR (CDCl3, 500 MHz) δ 10.30 (s, 1H), 7.78 (d, J=2.4 Hz, 1H), 7.77 (d, J=2.5 Hz, 1H). the ice bath was removed forming a white suspension The solids were removed by filtration The mother liquor was cooled to 0° C. The ice bath was removed stirring was continued for 30 min The resulting solid was collected by filtration dried in vacuo for several hours to afford 2.6 g (76%) as a white solid

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

Procedure: To a suspension of 2-amino-3-bromo-5-chlorobenzaldehyde (3.0 g, 12.8 mmol) in a water (4 mL) and hydrochloric acid (4 mL) mixture at 0° C. was added a solution of sodium nitrite (1.1 g, 16.0 mmol) in water (ca. 2 mL) dropwise. After 30 min, the ice bath was removed and the reaction stirred at room temperature for 30 min forming a white suspension. The solids were removed by filtration. The mother liquor was cooled to 0° C. and treated with sodium azide (0.8 g, 12.8 mmol) in water (2.0 mL). The ice bath was removed and stirring was continued for 30 min. The resulting solid was collected by filtration and dried in vacuo for several hours to afford 2.6 g (76%) as a white solid. 1H-NMR (CDCl3, 500 MHz) δ 10.30 (s, 1H), 7.78 (d, J=2.4 Hz, 1H), 7.77 (d, J=2.5 Hz, 1H). the ice bath was removed forming a white suspension The solids were removed by filtration The mother liquor was cooled to 0° C. The ice bath was removed stirring was continued for 30 min The resulting solid was collected by filtration dried in vacuo for several hours to afford 2.6 g (76%) as a white solid

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

Procedure: 2-Amino-5-chlorobenzaldehyde (2.1 g, 13.5 mmol) was dissolved in chloroform (20 mL) and treated with N-bromosuccinimide (2.6 g, 14.9 mmol). The reaction was stirred for 30 min at ambient temperature. The reaction was diluted with methylene chloride and washed with sodium thiosulfate (2×), 5% sodium bicarbonate (2×), water (2×), brine, dried over sodium sulfate, and concentrated to afford 3.0 g (95%) as a pale yellow powder. 1H-NMR (CDCl3, 500 MHz) δ 9.75 (s, 1H), 7.60 (d, J=2.4 Hz, 1H), 7.45 (d, J=2.4 Hz, 1H). Mass spec.: 236.01 (MH)+. washed with sodium thiosulfate (2×), 5% sodium bicarbonate (2×), water (2×), brine dried over sodium sulfate concentrated to afford 3.0 g (95%) as a pale yellow powder

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

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

Procedure: To a suspension of 2-amino-3-bromo-5-chlorobenzaldehyde (3.0 g, 12.8 mmol) in a water (4 mL) and hydrochloric acid (4 mL) mixture at 0° C. was added a solution of sodium nitrite (1.1 g, 16.0 mmol) in water (ca. 2 mL) dropwise. After 30 min, the ice bath was removed and the reaction stirred at room temperature for 30 min forming a white suspension. The solids were removed by filtration. The mother liquor was cooled to 0° C. and treated with sodium azide (0.8 g, 12.8 mmol) in water (2.0 mL). The ice bath was removed and stirring was continued for 30 min. The resulting solid was collected by filtration and dried in vacuo for several hours to afford 2.6 g (76%) as a white solid. 1H-NMR (CDCl3, 500 MHz) δ 10.30 (s, 1H), 7.78 (d, J=2.4 Hz, 1H), 7.77 (d, J=2.5 Hz, 1H). the ice bath was removed forming a white suspension The solids were removed by filtration The mother liquor was cooled to 0° C. The ice bath was removed stirring was continued for 30 min The resulting solid was collected by filtration dried in vacuo for several hours to afford 2.6 g (76%) as a white solid

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

Procedure: 2-Amino-5-chlorobenzaldehyde (2.1 g, 13.5 mmol) was dissolved in chloroform (20 mL) and treated with N-bromosuccinimide (2.6 g, 14.9 mmol). The reaction was stirred for 30 min at ambient temperature. The reaction was diluted with methylene chloride and washed with sodium thiosulfate (2×), 5% sodium bicarbonate (2×), water (2×), brine, dried over sodium sulfate, and concentrated to afford 3.0 g (95%) as a pale yellow powder. 1H-NMR (CDCl3, 500 MHz) δ 9.75 (s, 1H), 7.60 (d, J=2.4 Hz, 1H), 7.45 (d, J=2.4 Hz, 1H). Mass spec.: 236.01 (MH)+. washed with sodium thiosulfate (2×), 5% sodium bicarbonate (2×), water (2×), brine dried over sodium sulfate concentrated to afford 3.0 g (95%) as a pale yellow powder