3,5-dichloro-2-iodophenol

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: When the product of Step A was substituted for 3,5-dichloro-2-iodophenol in Example 8, Step E, the similar process afforded the title compound in 31%, as off-white oil. 1H-NMR (CDCl3) 0.93 (m, 3H); 1.58-1.73 (m, 2H); 1.9 (tr, 1H, J=6 Hz); 2.65 (tr, 2H, J=6 Hz); 4.76 (d, 2H, J=6 Hz); 6.58 (s, 1H); 7.08 (dd, 1H, J=3, 9 Hz); 7.3-7.37 (m, 2H).

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: When the product of Step A was substituted for 3,5-dichloro-2-iodophenol in Example 8, Step E, the similar process afforded the title compound in 31%, as off-white oil. 1H-NMR (CDCl3) 0.93 (m, 3H); 1.58-1.73 (m, 2H); 1.9 (tr, 1H, J=6 Hz); 2.65 (tr, 2H, J=6 Hz); 4.76 (d, 2H, J=6 Hz); 6.58 (s, 1H); 7.08 (dd, 1H, J=3, 9 Hz); 7.3-7.37 (m, 2H).

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Propargyl alcohol (0.12 ml; 1.96 mmol) was added drop wise to a refluxing mixture of the product of Step D (0.55 g; 1.96 mmol) and Cu2O (0.2 g; 1.4 mmol) in anhydrous pyridine (4 ml) under N2. After refluxing for 1 h, the solvent was removed under reduced pressure and the residue was treated with EtOAc (15 ml). The insoluble material was filtered off and the filtrate was washed with 10% citric acid, H2O, brine, dried over anhydrous MgSO4 and filtered. The filtrate was evaporated under reduced pressure and the residue was purified by FCC (SiO2; CH2Cl2) to give the title compound (0.24 g; 56%) as colourless solid. 1H-NMR (CDCl3) 1.91 (tr, 1H, J=6.3 Hz); 4.75 (d, 1H, J=6.3 Hz); 6.72 (s, 1H); 7.23 (s, 1H); 7.37 (s, 1H). After refluxing for 1 h the solvent was removed under reduced pressure the residue was treated with EtOAc (15 ml) The insoluble material was filtered off the filtrate was washed with 10% citric acid, H2O, brine dried over anhydrous MgSO4 filtered The filtrate was evaporated under reduced pressure the residue was purified by FCC (SiO2; CH2Cl2)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a suspension of 3,5-dichlorophenol (0.6 g; 3.68 mmol) in H2O (15 ml), 30% H2O2 was added followed by I2 (0.47 g; 1.85 mmol). The resulting mixture was vigorously stirred for 8 h at room temperature, then extracted with CH2Cl2 (15 ml) and the organic phase was dried over anhydrous MgSO4 and filtered. The filtrate was evaporated under reduced pressure and the residue was purified by FCC (SiO2; CH2Cl2) to give the title compound (0.55 g; 52%) as colourless solid. 1H-NMR (CDCl3) 5.58 (s, 1H); 6.89 (s, 1H); 7.06 (s, 1H). was added extracted with CH2Cl2 (15 ml) the organic phase was dried over anhydrous MgSO4 filtered The filtrate was evaporated under reduced pressure the residue was purified by FCC (SiO2; CH2Cl2)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: When the product of Step A was substituted for 3,5-dichloro-2-iodophenol in Example 8, Step E, the similar process afforded the title compound in 31%, as off-white oil. 1H-NMR (CDCl3) 0.93 (m, 3H); 1.58-1.73 (m, 2H); 1.9 (tr, 1H, J=6 Hz); 2.65 (tr, 2H, J=6 Hz); 4.76 (d, 2H, J=6 Hz); 6.58 (s, 1H); 7.08 (dd, 1H, J=3, 9 Hz); 7.3-7.37 (m, 2H).

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Propargyl alcohol (0.12 ml; 1.96 mmol) was added drop wise to a refluxing mixture of the product of Step D (0.55 g; 1.96 mmol) and Cu2O (0.2 g; 1.4 mmol) in anhydrous pyridine (4 ml) under N2. After refluxing for 1 h, the solvent was removed under reduced pressure and the residue was treated with EtOAc (15 ml). The insoluble material was filtered off and the filtrate was washed with 10% citric acid, H2O, brine, dried over anhydrous MgSO4 and filtered. The filtrate was evaporated under reduced pressure and the residue was purified by FCC (SiO2; CH2Cl2) to give the title compound (0.24 g; 56%) as colourless solid. 1H-NMR (CDCl3) 1.91 (tr, 1H, J=6.3 Hz); 4.75 (d, 1H, J=6.3 Hz); 6.72 (s, 1H); 7.23 (s, 1H); 7.37 (s, 1H). After refluxing for 1 h the solvent was removed under reduced pressure the residue was treated with EtOAc (15 ml) The insoluble material was filtered off the filtrate was washed with 10% citric acid, H2O, brine dried over anhydrous MgSO4 filtered The filtrate was evaporated under reduced pressure the residue was purified by FCC (SiO2; CH2Cl2)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a suspension of 3,5-dichlorophenol (0.6 g; 3.68 mmol) in H2O (15 ml), 30% H2O2 was added followed by I2 (0.47 g; 1.85 mmol). The resulting mixture was vigorously stirred for 8 h at room temperature, then extracted with CH2Cl2 (15 ml) and the organic phase was dried over anhydrous MgSO4 and filtered. The filtrate was evaporated under reduced pressure and the residue was purified by FCC (SiO2; CH2Cl2) to give the title compound (0.55 g; 52%) as colourless solid. 1H-NMR (CDCl3) 5.58 (s, 1H); 6.89 (s, 1H); 7.06 (s, 1H). was added extracted with CH2Cl2 (15 ml) the organic phase was dried over anhydrous MgSO4 filtered The filtrate was evaporated under reduced pressure the residue was purified by FCC (SiO2; CH2Cl2)