2-chloro-5-iodophenol

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A suspension of 300 g (1179 mmol) of 2-chloro-5-iodophenol, 184 g (1179 mmol) of 4-methoxybenzyl chloride and 195.5 g (1415 mmol) of anhydrous K2CO3 in 1.2 L of anhydrous DMF is stirred for 5 hours at 70° C. and then cooled to room temperature. The reaction medium is then poured into 3 L of a 2/1 ether/water mixture. The organic phase is washed with 2×1 L of water, dried over Na2SO4 and concentrated under reduced pressure, and the residue obtained is solidified in pentane. 406 g of 2-[(4-methoxybenzyl)oxy]-1-chloro-4-iodobenzene are thus obtained in the form of a beige-colored powder. cooled to room temperature The organic phase is washed with 2×1 L of water dried over Na2SO4 concentrated under reduced pressure the residue obtained

反応条件: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A suspension of 300 g (1179 mmol) of 2-chloro-5-iodophenol, 184 g (1179 mmol) of 4-methoxybenzyl chloride and 195.5 g (1415 mmol) of anhydrous K2CO3 in 1.2 L of anhydrous DMF is stirred for 5 hours at 70° C. and then cooled to room temperature. The reaction medium is then poured into 3 L of a 2/1 ether/water mixture. The organic phase is washed with 2×1 L of water, dried over Na2SO4 and concentrated under reduced pressure, and the residue obtained is solidified in pentane. 406 g of 2-[(4-methoxybenzyl)oxy]-1-chloro-4-iodobenzene are thus obtained in the form of a beige-colored powder. cooled to room temperature The organic phase is washed with 2×1 L of water dried over Na2SO4 concentrated under reduced pressure the residue obtained

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 2-Chloro-5-iodophenol (2.50 g, 9.83 mmol), tert-butyl 4-hydroxy-1-piperidinecarboxylate (2.97 g, 14.7 mmol) and triphenylphosphine (5.15 g, 19.6 mmol), were suspended in THF (50 mL) and cooled to 0° C. Diethyl azodicarboxylate (3.08 mL, 19.6 mmol) was then added dropwise, the reaction was stirred under a N2 atmosphere for 18 h. The reaction was then partitioned between H2O and EtOAc. The organic layer was separated, washed with saturated brine, dried over MgSO4, concentrated in vacuo and subjected to FCC, eluting with 0-50% EtOAc/cyclohexane, to afford the title compound (3.43 g, 80%). (Method 3): Rt 4.98 min, m/z 337.9 [M−BOC+]. The reaction was then partitioned between H2O and EtOAc The organic layer was separated washed with saturated brine dried over MgSO4 concentrated in vacuo eluting with 0-50% EtOAc/cyclohexane

反応条件: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A suspension of 300 g (1179 mmol) of 2-chloro-5-iodophenol, 184 g (1179 mmol) of 4-methoxybenzyl chloride and 195.5 g (1415 mmol) of anhydrous K2CO3 in 1.2 L of anhydrous DMF is stirred for 5 hours at 70° C. and then cooled to room temperature. The reaction medium is then poured into 3 L of a 2/1 ether/water mixture. The organic phase is washed with 2×1 L of water, dried over Na2SO4 and concentrated under reduced pressure, and the residue obtained is solidified in pentane. 406 g of 2-[(4-methoxybenzyl)oxy]-1-chloro-4-iodobenzene are thus obtained in the form of a beige-colored powder. cooled to room temperature The organic phase is washed with 2×1 L of water dried over Na2SO4 concentrated under reduced pressure the residue obtained

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 2-Chloro-5-iodophenol (2.50 g, 9.83 mmol), tert-butyl 4-hydroxy-1-piperidinecarboxylate (2.97 g, 14.7 mmol) and triphenylphosphine (5.15 g, 19.6 mmol), were suspended in THF (50 mL) and cooled to 0° C. Diethyl azodicarboxylate (3.08 mL, 19.6 mmol) was then added dropwise, the reaction was stirred under a N2 atmosphere for 18 h. The reaction was then partitioned between H2O and EtOAc. The organic layer was separated, washed with saturated brine, dried over MgSO4, concentrated in vacuo and subjected to FCC, eluting with 0-50% EtOAc/cyclohexane, to afford the title compound (3.43 g, 80%). (Method 3): Rt 4.98 min, m/z 337.9 [M-BOC+]. The reaction was then partitioned between H2O and EtOAc The organic layer was separated washed with saturated brine dried over MgSO4 concentrated in vacuo eluting with 0-50% EtOAc/cyclohexane

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 2-Chloro-5-iodophenol (2.50 g, 9.83 mmol), tert-butyl 4-hydroxy-1-piperidinecarboxylate (2.97 g, 14.7 mmol) and triphenylphosphine (5.15 g, 19.6 mmol), were suspended in THF (50 mL) and cooled to 0° C. Diethyl azodicarboxylate (3.08 mL, 19.6 mmol) was then added dropwise, the reaction was stirred under a N2 atmosphere for 18 h. The reaction was then partitioned between H2O and EtOAc. The organic layer was separated, washed with saturated brine, dried over MgSO4, concentrated in vacuo and subjected to FCC, eluting with 0-50% EtOAc/cyclohexane, to afford the title compound (3.43 g, 80%). (Method 3): Rt 4.98 min, m/z 337.9 [M-BOC+]. The reaction was then partitioned between H2O and EtOAc The organic layer was separated washed with saturated brine dried over MgSO4 concentrated in vacuo eluting with 0-50% EtOAc/cyclohexane

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

実験手順: To a solution of 2-chloro-5-iodophenol (509 mg, 2.00 mmol) in dimethylformamide were added potassium carbonate (415 mg, 3.00 mmol) and t-butyl bromoacetate (0.440 ml, 3.00 mmol) and the mixture was stirred for 1 hour at room temperature. Thereto was added water and the mixture was extracted with ethyl acetate. The organic layer was washed with 10% aqueous citric acid solution, water, an aqueous saturated sodium hydrogencarbonate solution and an aqueous saturated sodium chloride solution in the order, and dried over magnesium sulfate. The solvent was removed and purified with silica gel chromatography (hexane:ethyl acetate, 20:1) to give t-butyl (2-chloro-5-iodophenoxy)acetate (851 mg, quantitatively) as a colorless oil. the mixture was extracted with ethyl acetate The organic layer was washed with 10% aqueous citric acid solution, water an aqueous saturated sodium hydrogencarbonate solution and an aqueous saturated sodium chloride solution in the order, and dried over magnesium sulfate The solvent was removed purified with silica gel chromatography (hexane:ethyl acetate, 20:1)

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

実験手順: To a solution of 1-chloro-4-iodo-2-methoxybenzene (1.34 g, 5 mmol) in dichloromethane was dropped under ice cooling a solution of 0.91M boron tribromide in dichloromethane (6.6 ml, 6.00 mmol) and the mixture was reacted for 1 hour under ice cooling and then for 3 days at room temperature. To the mixture was added an aqueous sodium hydrogencarbonate solution and then the mixture was acidified with concentrated hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with an aqueous saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was removed and purified with silica gel chromatography (hexane:ethyl acetate, 10:1) to give the subject compound (1.11 g, 87%) as white crystals. the mixture was reacted for 1 hour under ice cooling followed by extraction with ethyl acetate The organic layer was washed with an aqueous saturated sodium chloride solution dried over anhydrous magnesium sulfate The solvent was removed purified with silica gel chromatography (hexane:ethyl acetate, 10:1)

反応条件: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A suspension of 300 g (1179 mmol) of 2-chloro-5-iodophenol, 184 g (1179 mmol) of 4-methoxybenzyl chloride and 195.5 g (1415 mmol) of anhydrous K2CO3 in 1.2 L of anhydrous DMF is stirred for 5 hours at 70° C. and then cooled to room temperature. The reaction medium is then poured into 3 L of a 2/1 ether/water mixture. The organic phase is washed with 2×1 L of water, dried over Na2SO4 and concentrated under reduced pressure, and the residue obtained is solidified in pentane. 406 g of 2-[(4-methoxybenzyl)oxy]-1-chloro-4-iodobenzene are thus obtained in the form of a beige-colored powder. cooled to room temperature The organic phase is washed with 2×1 L of water dried over Na2SO4 concentrated under reduced pressure the residue obtained

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 2-Chloro-5-iodophenol (2.50 g, 9.83 mmol), tert-butyl 4-hydroxy-1-piperidinecarboxylate (2.97 g, 14.7 mmol) and triphenylphosphine (5.15 g, 19.6 mmol), were suspended in THF (50 mL) and cooled to 0° C. Diethyl azodicarboxylate (3.08 mL, 19.6 mmol) was then added dropwise, the reaction was stirred under a N2 atmosphere for 18 h. The reaction was then partitioned between H2O and EtOAc. The organic layer was separated, washed with saturated brine, dried over MgSO4, concentrated in vacuo and subjected to FCC, eluting with 0-50% EtOAc/cyclohexane, to afford the title compound (3.43 g, 80%). (Method 3): Rt 4.98 min, m/z 337.9 [M−BOC+]. The reaction was then partitioned between H2O and EtOAc The organic layer was separated washed with saturated brine dried over MgSO4 concentrated in vacuo eluting with 0-50% EtOAc/cyclohexane