ethyl 2-(3-bromophenyl)-2-oxoacetate

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

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

Procedure: A suspension of (3-bromo-phenyl)-oxo-acetic acid ethyl ester (2.0 g, 7.8 mmol), dimethylamine (19.5 mL, 2 N in THF, 39 mmol), and sodium triacetoxyborohydride (4.95 g, 23.4 mmol) in 1,2-dichloroethane (40 mL) was stirred at room temperature for 36 hours. Satuated sodium bicarbonate (50 mL) was added and the resulting mixture was extracted with ethyl acetate. The combined organic extracts were dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography on silica gel using a gradient of methanol in dichloromethane to afford (3-bromo-phenyl)-dimethylamino-acetic acid ethyl ester (350 mg, 16%) as an oil. MS: m/z 286 (M+H+). the resulting mixture was extracted with ethyl acetate The combined organic extracts were dried over sodium sulfate filtered concentrated The residue was purified by flash chromatography on silica gel using a gradient of methanol in dichloromethane

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

Procedure: A suspension of (3-bromo-phenyl)-oxo-acetic acid ethyl ester (2.0 g, 7.8 mmol), dimethylamine (19.5 mL, 2 N in THF, 39 mmol), and sodium triacetoxyborohydride (4.95 g, 23.4 mmol) in 1,2-dichloroethane (40 mL) was stirred at room temperature for 36 hours. Satuated sodium bicarbonate (50 mL) was added and the resulting mixture was extracted with ethyl acetate. The combined organic extracts were dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography on silica gel using a gradient of methanol in dichloromethane to afford (3-bromo-phenyl)-dimethylamino-acetic acid ethyl ester (350 mg, 16%) as an oil. MS: m/z 286 (M+H+). the resulting mixture was extracted with ethyl acetate The combined organic extracts were dried over sodium sulfate filtered concentrated The residue was purified by flash chromatography on silica gel using a gradient of methanol in dichloromethane

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

Procedure: To a solution of (3-Bromo-phenyl)-oxo-acetic acid ethyl ester (1 g, 3.9 mmol) in methanol (10 mL) was added potassium hydroxide (2 mL, 50% w/v in water) and the resulting mixture was stirred at room temperature for 30 minutes. Hydrochloric acid (1 N) was added to adjust to pH 4. The mixture was extracted with ethyl acetate (5 mL×4) and the combined organic extracts were dried over sodium sulfate, filtered, and concentrated. The residue was used in next step without further purification (0.8 g, 89% yield). MS: m/z 230 (M−H+). The mixture was extracted with ethyl acetate (5 mL×4) the combined organic extracts were dried over sodium sulfate filtered concentrated The residue was used in next step without further purification (0.8 g, 89% yield)

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

Procedure: To a solution of (3-Bromo-phenyl)-oxo-acetic acid ethyl ester (2.5 g, 9.8 mmol) in ether (20 mL) at 0° C. was added methyl magnesium bromide (10.8 mmol, 3 M in ether, 3.6 mL) with stirring. The reaction was stirred at 0° C. for 15 min. Water was added and the crude partitioned between ethyl acetate and water. The aqueous layer was extracted three times with ethyl acetate and the combined organic layers were washed with brine, dried over sodium sulfate and evaporated. The resulting crude was purified by flash chromatography on silica gel using a gradient of ethyl acetate in hexane to afford 2-(3-bromo-phenyl)-2-hydroxy-propionic acid ethyl ester as a colorless liquid. (1.87 g, 70% yield). MS: m/z 273 (M+H+). The reaction was stirred at 0° C. for 15 min the crude partitioned between ethyl acetate and water The aqueous layer was extracted three times with ethyl acetate the combined organic layers were washed with brine dried over sodium sulfate evaporated The resulting crude was purified by flash chromatography on silica gel using a gradient of ethyl acetate in hexane

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

Procedure: To a solution of (3-Bromo-phenyl)-oxo-acetic acid ethyl ester (2.5 g, 9.8 mmol) in ether (20 mL) at 0° C. was added methyl magnesium bromide (10.8 mmol, 3 M in ether, 3.6 mL) with stirring. The reaction was stirred at 0° C. for 15 min. Water was added and the crude partitioned between ethyl acetate and water. The aqueous layer was extracted three times with ethyl acetate and the combined organic layers were washed with brine, dried over sodium sulfate and evaporated. The resulting crude was purified by flash chromatography on silica gel using a gradient of ethyl acetate in hexane to afford 2-(3-bromo-phenyl)-2-hydroxy-propionic acid ethyl ester as a colorless liquid. (1.87 g, 70% yield). MS: m/z 273 (M+H+). The reaction was stirred at 0° C. for 15 min the crude partitioned between ethyl acetate and water The aqueous layer was extracted three times with ethyl acetate the combined organic layers were washed with brine dried over sodium sulfate evaporated The resulting crude was purified by flash chromatography on silica gel using a gradient of ethyl acetate in hexane

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

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

Procedure: A suspension of (3-bromo-phenyl)-oxo-acetic acid ethyl ester (2.0 g, 7.8 mmol), dimethylamine (19.5 mL, 2 N in THF, 39 mmol), and sodium triacetoxyborohydride (4.95 g, 23.4 mmol) in 1,2-dichloroethane (40 mL) was stirred at room temperature for 36 hours. Satuated sodium bicarbonate (50 mL) was added and the resulting mixture was extracted with ethyl acetate. The combined organic extracts were dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography on silica gel using a gradient of methanol in dichloromethane to afford (3-bromo-phenyl)-dimethylamino-acetic acid ethyl ester (350 mg, 16%) as an oil. MS: m/z 286 (M+H+). the resulting mixture was extracted with ethyl acetate The combined organic extracts were dried over sodium sulfate filtered concentrated The residue was purified by flash chromatography on silica gel using a gradient of methanol in dichloromethane

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

Procedure: To a solution of (3-Bromo-phenyl)-oxo-acetic acid ethyl ester (1 g, 3.9 mmol) in methanol (10 mL) was added potassium hydroxide (2 mL, 50% w/v in water) and the resulting mixture was stirred at room temperature for 30 minutes. Hydrochloric acid (1 N) was added to adjust to pH 4. The mixture was extracted with ethyl acetate (5 mL×4) and the combined organic extracts were dried over sodium sulfate, filtered, and concentrated. The residue was used in next step without further purification (0.8 g, 89% yield). MS: m/z 230 (M−H+). The mixture was extracted with ethyl acetate (5 mL×4) the combined organic extracts were dried over sodium sulfate filtered concentrated The residue was used in next step without further purification (0.8 g, 89% yield)

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

Procedure: To a solution of (3-Bromo-phenyl)-oxo-acetic acid ethyl ester (2.5 g, 9.8 mmol) in ether (20 mL) at 0° C. was added methyl magnesium bromide (10.8 mmol, 3 M in ether, 3.6 mL) with stirring. The reaction was stirred at 0° C. for 15 min. Water was added and the crude partitioned between ethyl acetate and water. The aqueous layer was extracted three times with ethyl acetate and the combined organic layers were washed with brine, dried over sodium sulfate and evaporated. The resulting crude was purified by flash chromatography on silica gel using a gradient of ethyl acetate in hexane to afford 2-(3-bromo-phenyl)-2-hydroxy-propionic acid ethyl ester as a colorless liquid. (1.87 g, 70% yield). MS: m/z 273 (M+H+). The reaction was stirred at 0° C. for 15 min the crude partitioned between ethyl acetate and water The aqueous layer was extracted three times with ethyl acetate the combined organic layers were washed with brine dried over sodium sulfate evaporated The resulting crude was purified by flash chromatography on silica gel using a gradient of ethyl acetate in hexane

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