1-(4,5-二氯-2-羟基-3-碘苯基)乙酮

反应条件: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of 1-(4,5-dichloro-2-hydroxy-3-iodophenyl)ethanone (16 g, 47 mmol) and potassium carbonate (17 g, 120 mmol) in DMF (40 mL) was treated with methyl iodide (6.4 mL, 100 mmol) and stirred at 60° C. for 1 hour. The reaction mixture was diluted with water and extracted with EtOAc (twice). The combined organic layers were dried with magnesium sulfate, filtered, and concentrated to give a crude solid. The crude material was purified by flash column chromatography using EtOAc in hexanes (5%-30%) to give the desired product (14 g, 84%) as an orange solid. LCMS for C9H8Cl2IO2 (M+H)+: m/z=344.9, 346.9. Found: 344.8, 346.9. extracted with EtOAc (twice) The combined organic layers were dried with magnesium sulfate filtered concentrated to give a crude solid The crude material was purified by flash column chromatography

反应条件: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of 1-(4,5-dichloro-2-hydroxy-3-iodophenyl)ethanone (16 g, 47 mmol) and potassium carbonate (17 g, 120 mmol) in DMF (40 mL) was treated with methyl iodide (6.4 mL, 100 mmol) and stirred at 60° C. for 1 hour. The reaction mixture was diluted with water and extracted with EtOAc (twice). The combined organic layers were dried with magnesium sulfate, filtered, and concentrated to give a crude solid. The crude material was purified by flash column chromatography using EtOAc in hexanes (5%-30%) to give the desired product (14 g, 84%) as an orange solid. LCMS for C9H8Cl2IO2 (M+H)+: m/z=344.9, 346.9. Found: 344.8, 346.9. extracted with EtOAc (twice) The combined organic layers were dried with magnesium sulfate filtered concentrated to give a crude solid The crude material was purified by flash column chromatography

反应条件: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of 1-(4,5-dichloro-2-hydroxyphenyl)ethanone (12 g, 59 mmol) in acetic acid (70 mL) was treated with N-iodosuccinimide (16 g, 71 mmol) and stirred at 90° C. for 18 hours. The reaction mixture was treated with additional N-iodosuccinimide (8 g, 36 mmol) and stirred at 90° C. for 4 hours. The reaction mixture was concentrated, diluted with EtOAc, and quenched with saturated sodium bicarbonate until the bubbling stopped. The organic layer was separated and the aqueous phase was re-extracted with EtOAc. The combined organic layers were dried and concentrated to give a brown solid. This material was recrystallized from methanol to give desired product (9.0 g, 46%) as a tan solid. LCMS for C8H6Cl2IO2 (M+H)+: m/z=330.9, 332.9. Found: 330.8, 332.9. stirred at 90° C. for 4 hours The reaction mixture was concentrated diluted with EtOAc quenched with saturated sodium bicarbonate until the bubbling The organic layer was separated the aqueous phase was re-extracted with EtOAc The combined organic layers were dried concentrated to give a brown solid This material was recrystallized from methanol

反应条件: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of 1-(4,5-dichloro-2-hydroxy-3-iodophenyl)ethanone (4.9 g, 15 mmol), triphenylphosphine (5.5 g, 21 mmol), and methanol (0.91 mL, 22 mmol) in tetrahydrofuran (44 mL) at 0° C. was treated with diisopropyl azodicarboxylate (4.1 mL, 21 mmol) dropwise and stirred at 20° C. for 16 h. The reaction mixture was concentrated, diluted with ethyl acetate, and poured into water. The organic layer was separated, washed with brine, dried with magnesium sulfate, filtered, and concentrated to a crude residue. Purification by flash column chromatography using ethyl acetate in hexanes (5%-30%) gave the desired product (4.1 g, 79%). LCMS for C9H8Cl2IO2 (M+H)+: m/z=344.9, 346.9. Found: 344.9, 346.7. The reaction mixture was concentrated diluted with ethyl acetate poured into water The organic layer was separated washed with brine dried with magnesium sulfate filtered concentrated to a crude residue Purification by flash column chromatography

反应条件: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of 1-(4,5-dichloro-2-hydroxy-3-iodophenyl)ethanone (4.9 g, 15 mmol), triphenylphosphine (5.5 g, 21 mmol), and methanol (0.91 mL, 22 mmol) in tetrahydrofuran (44 mL) at 0° C. was treated with diisopropyl azodicarboxylate (4.1 mL, 21 mmol) dropwise and stirred at 20° C. for 16 h. The reaction mixture was concentrated, diluted with ethyl acetate, and poured into water. The organic layer was separated, washed with brine, dried with magnesium sulfate, filtered, and concentrated to a crude residue. Purification by flash column chromatography using ethyl acetate in hexanes (5%-30%) gave the desired product (4.1 g, 79%). LCMS for C9H8Cl2IO2 (M+H)+: m/z=344.9, 346.9. Found: 344.9, 346.7. The reaction mixture was concentrated diluted with ethyl acetate poured into water The organic layer was separated washed with brine dried with magnesium sulfate filtered concentrated to a crude residue Purification by flash column chromatography

反应条件: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of 1-(4,5-dichloro-2-hydroxy-3-iodophenyl)ethanone (4.9 g, 15 mmol), triphenylphosphine (5.5 g, 21 mmol), and methanol (0.91 mL, 22 mmol) in tetrahydrofuran (44 mL) at 0° C. was treated with diisopropyl azodicarboxylate (4.1 mL, 21 mmol) dropwise and stirred at 20° C. for 16 h. The reaction mixture was concentrated, diluted with ethyl acetate, and poured into water. The organic layer was separated, washed with brine, dried with magnesium sulfate, filtered, and concentrated to a crude residue. Purification by flash column chromatography using ethyl acetate in hexanes (5%-30%) gave the desired product (4.1 g, 79%). LCMS for C9H8Cl2IO2 (M+H)+: m/z=344.9, 346.9. Found: 344.9, 346.7. The reaction mixture was concentrated diluted with ethyl acetate poured into water The organic layer was separated washed with brine dried with magnesium sulfate filtered concentrated to a crude residue Purification by flash column chromatography

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: The desired compound was prepared according to the procedure of Example 6, Step 2, using 1-(4,5-dichloro-2-hydroxyphenyl)ethanone and N-iodosuccinimide (instead of N-bromosuccinimide) as the starting materials in 71% yield. LCMS for C8H6Cl2IO2 (M+H)+: m/z=330.9, 332.9. Found: 330.8, 332.9.

反应条件: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of 1-(4,5-dichloro-2-hydroxy-3-iodophenyl)ethanone (16 g, 47 mmol) and potassium carbonate (17 g, 120 mmol) in N,N-dimethylformamide (40 mL)was treated with methyl iodide (6.4 mL, 100 mmol) and stirred at 60° C. for 1 h. The reaction mixture was diluted with water and extracted with ethyl acetate (2×). The combined organic layers were dried with magnesium sulfate, filtered, and concentrated to give a crude solid. The crude material was purified by flash column chromatography using ethyl acetate in hexanes (5%-30%) to give the desired product (14 g, 84%) as an orange solid. 1H NMR (300 MHz, CDCl3) δ 7.69 (s, 1H), 3.79 (s, 3H), 2.60 (s, 3H). LCMS for C9H8Cl2IO2 (M+H)+: m/z=344.9, 346.9; Found: 344.8, 346.9. extracted with ethyl acetate (2×) The combined organic layers were dried with magnesium sulfate filtered concentrated to give a crude solid The crude material was purified by flash column chromatography

反应条件: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of 1-(4,5-dichloro-2-hydroxyphenyl)ethanone (12 g, 59 mmol) in acetic acid (70 mL) was treated with N-iodosuccinimide (16 g, 71 mmol) and stirred at 90° C. for 18 h. The reaction mixture was treated with additional N-iodosuccinimide (8 g, 36 mmol) and stirred at 90° C. for 4 h. The reaction mixture was concentrated, diluted with ethyl acetate, and quenched with saturated sodium bicarbonate until the bubbling stopped. The organic layer was separated and the aqueous was re-extracted with ethyl acetate. The combined organic layers were dried and concentrated to give a brown solid. This material was recrystallized from methanol to give desired product (9.0 g, 46%) as a tan solid. 1H NMR (300 MHz, CDCl3) δ 13.36 (s, 1H), 7.85 (s, 1H), 2.65 (s, 3H). LCMS for C8H6Cl2IO2 (M+H)+: m/z=330.9, 332.9; Found: 330.8, 332.9. stirred at 90° C. for 4 h The reaction mixture was concentrated diluted with ethyl acetate quenched with saturated sodium bicarbonate until the bubbling The organic layer was separated the aqueous was re-extracted with ethyl acetate The combined organic layers were dried concentrated to give a brown solid This material was recrystallized from methanol

反应条件: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of 1-(4,5-dichloro-2-hydroxy-3-iodophenyl)ethanone (16 g, 47 mmol) and potassium carbonate (17 g, 120 mmol) in DMF (40 mL) was treated with methyl iodide (6.4 mL, 100 mmol) and stirred at 60° C. for 1 hour. The reaction mixture was diluted with water and extracted with EtOAc (twice). The combined organic layers were dried with magnesium sulfate, filtered, and concentrated to give a crude solid. The crude material was purified by flash column chromatography using EtOAc in hexanes (5%-30%) to give the desired product (14 g, 84%) as an orange solid. LCMS for C9H8Cl2IO2 (M+H)+: m/z=344.9, 346.9. Found: 344.8, 346.9. extracted with EtOAc (twice) The combined organic layers were dried with magnesium sulfate filtered concentrated to give a crude solid The crude material was purified by flash column chromatography

反应条件: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of 1-(4,5-dichloro-2-hydroxyphenyl)ethanone (12 g, 59 mmol) in acetic acid (70 mL) was treated with N-iodosuccinimide (16 g, 71 mmol) and stirred at 90° C. for 18 hours. The reaction mixture was treated with additional N-iodosuccinimide (8 g, 36 mmol) and stirred at 90° C. for 4 hours. The reaction mixture was concentrated, diluted with EtOAc, and quenched with saturated sodium bicarbonate until the bubbling stopped. The organic layer was separated and the aqueous phase was re-extracted with EtOAc. The combined organic layers were dried and concentrated to give a brown solid. This material was recrystallized from methanol to give desired product (9.0 g, 46%) as a tan solid. LCMS for C8H6Cl2IO2 (M+H)+: m/z=330.9, 332.9. Found: 330.8, 332.9. stirred at 90° C. for 4 hours The reaction mixture was concentrated diluted with EtOAc quenched with saturated sodium bicarbonate until the bubbling The organic layer was separated the aqueous phase was re-extracted with EtOAc The combined organic layers were dried concentrated to give a brown solid This material was recrystallized from methanol