1-(3-bromo-5-chloro-2-hydroxyphenyl)ethanone

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A suspension of 3′-bromo-5′-chloro-2′-hydroxyacetophenone (2.4 g, 10 mmol), potassium carbonate (2.8 g, 20 mmol) and 1,2-dibromoethane (3.5 mL, 41 mmol) in anhydrous N,N-dimethylformamide (30 mL) was stirred at 50° C. overnight. After cooling, the reaction mixture was diluted with water (100 mL), and the whole was extracted with ethyl acetate (100 mL). The organic layer was washed with saturated aqueous ammonium chloride solution (50 mL, twice) and brine (50 mL) and dried over anhydrous magnesium sulfate. The solvent was removed in vacuo to give the title reference compound (4.4 g) as orange oil (Quantitative). After cooling the whole was extracted with ethyl acetate (100 mL) The organic layer was washed with saturated aqueous ammonium chloride solution (50 mL twice) and brine (50 mL) and dried over anhydrous magnesium sulfate The solvent was removed in vacuo

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 1-(3-bromo-5-chloro-2-hydroxyphenyl)ethanone (5.0 g, 20 mmol) in N,N-dimethylformamide (40 mL) was treated with potassium carbonate (5.5 g, 40 mmol) followed by methyl iodide (1.9 mL, 30 mmol) and heated at 60° C. overnight. The reaction mixture was diluted with water (300 mL) and extracted with ethyl acetate (2×150 mL). The organic layers were washed with water (3×100 mL) and brine, dried with sodium sulfate, filtered, and concentrated to give the crude product. Purification by flash column chromatography using ethyl acetate in hexanes (0%-5%-25%) gave the desired product (5.1 g, 96%). LCMS for C9H9BrClO2 (M+H)+: m/z=262.9, 264.9. Found: 262.9, 264.9. extracted with ethyl acetate (2×150 mL) The organic layers were washed with water (3×100 mL) and brine dried with sodium sulfate filtered concentrated to give the crude product Purification by flash column chromatography

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A suspension of 3′-bromo-5′-chloro-2′-hydroxyacetophenone (2.4 g, 10 mmol), potassium carbonate (2.8 g, 20 mmol) and 1,2-dibromoethane (3.5 mL, 41 mmol) in anhydrous N,N-dimethylformamide (30 mL) was stirred at 50° C. overnight. After cooling, the reaction mixture was diluted with water (100 mL), and the whole was extracted with ethyl acetate (100 mL). The organic layer was washed with saturated aqueous ammonium chloride solution (50 mL, twice) and brine (50 mL) and dried over anhydrous magnesium sulfate. The solvent was removed in vacuo to give the title reference compound (4.4 g) as orange oil (Quantitative). After cooling the whole was extracted with ethyl acetate (100 mL) The organic layer was washed with saturated aqueous ammonium chloride solution (50 mL twice) and brine (50 mL) and dried over anhydrous magnesium sulfate The solvent was removed in vacuo

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A suspension of 3′-bromo-5′-chloro-2′-hydroxyacetophenone (2.4 g, 10 mmol), potassium carbonate (2.8 g, 20 mmol) and 1,2-dibromoethane (3.5 mL, 41 mmol) in anhydrous N,N-dimethylformamide (30 mL) was stirred at 50° C. overnight. After cooling, the reaction mixture was diluted with water (100 mL), and the whole was extracted with ethyl acetate (100 mL). The organic layer was washed with saturated aqueous ammonium chloride solution (50 mL, twice) and brine (50 mL) and dried over anhydrous magnesium sulfate. The solvent was removed in vacuo to give the title reference compound (4.4 g) as orange oil (Quantitative). After cooling the whole was extracted with ethyl acetate (100 mL) The organic layer was washed with saturated aqueous ammonium chloride solution (50 mL twice) and brine (50 mL) and dried over anhydrous magnesium sulfate The solvent was removed in vacuo

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 1-(3-bromo-5-chloro-2-hydroxyphenyl)ethanone (5.0 g, 20 mmol) in N,N-dimethylformamide (40 mL) was treated with potassium carbonate (5.5 g, 40 mmol) followed by methyl iodide (1.9 mL, 30 mmol) and heated at 60° C. overnight. The reaction mixture was diluted with water (300 mL) and extracted with ethyl acetate (2×150 mL). The organic layers were washed with water (3×100 mL) and brine, dried with sodium sulfate, filtered, and concentrated to give the crude product. Purification by flash column chromatography using ethyl acetate in hexanes (0%-5%-25%) gave the desired product (5.1 g, 96%). LCMS for C9H9BrClO2 (M+H)+: m/z=262.9, 264.9. Found: 262.9, 264.9. extracted with ethyl acetate (2×150 mL) The organic layers were washed with water (3×100 mL) and brine dried with sodium sulfate filtered concentrated to give the crude product Purification by flash column chromatography

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A suspension of 3′-bromo-5′-chloro-2′-hydroxyacetophenone (2.4 g, 10 mmol), potassium carbonate (2.8 g, 20 mmol) and 1,2-dibromoethane (3.5 mL, 41 mmol) in anhydrous N,N-dimethylformamide (30 mL) was stirred at 50° C. overnight. After cooling, the reaction mixture was diluted with water (100 mL), and the whole was extracted with ethyl acetate (100 mL). The organic layer was washed with saturated aqueous ammonium chloride solution (50 mL, twice) and brine (50 mL) and dried over anhydrous magnesium sulfate. The solvent was removed in vacuo to give the title reference compound (4.4 g) as orange oil (Quantitative). After cooling the whole was extracted with ethyl acetate (100 mL) The organic layer was washed with saturated aqueous ammonium chloride solution (50 mL twice) and brine (50 mL) and dried over anhydrous magnesium sulfate The solvent was removed in vacuo