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Under nitrogen atmosphere, 10 ml of a solution of 1.6M n-butyl lithium (16 mmol) in hexane is put into a 100 ml three-necked flask cooled at -80 C. After cooling to -80 C., 10 ml of THF is added dropwise thereto using a dropping funnel while the THF is maintained at -60 C. Thereafter, 3.1 g (16 mmol) of 1-bromo-4-n-octylbenzene maintained at -60 C. is added dropwise thereto using a dropping funnel. The resultant mixture is stirred at -40 C. for 1 hour, and a solution of 2.3 g (22 mmol) of trimethyl borate in 10 ml of THF is added dropwise to the mixture using a dropping funnel while the temperature of the added solution is maintained at -40 C. Thereafter, the temperature of the mixture is gradually increased to 10 C. over 2 hours, and 50 ml of a 10% HCl aqueous solution is added thereto at 0 C., and extraction is performed using 100 ml of toluene. The extract is washed with 100 ml of pure water three times, and is dehydrated using sodium sulfate. Toluene is distilled off by reducing the pressure, whereby remaining matter in an amount of 3.3 g is obtained. The remaining matter is washed with a mixed solution of 100 ml pure water/100 ml hexane, whereby 2.0 g of Compound V-a, which is 4-n-octylphenyl borate, is obtained. The obtained compound is identified as the desired product by 1H-NMR and IR.
With hydrogenchloride; n-butyllithium; In tetrahydrofuran; hexane;
Synthesis Example 2 Synthesis of Exemplified Compound 4 <Synthesis of Compound V-a> In a nitrogen atmosphere, 10 ml (16 mmol) of a 1.6 M n-butyllithium/hexane solution is added to a 100-ml three-necked flask cooled to -80 C. This solution is cooled to -80 C., and then 10 ml of THF maintained at -60 C. is added dropwise thereto from a dropping funnel. Subsequently, 3.1 g (16 mmol) of 1-bromo-4-n-octylbenzene maintained at -60 C. is added dropwise to the mixture from a dropping funnel. This mixture is stirred for one hour at -40 C., and then a solution of 2.3 g (22 mmol) of trimethyl borate in THF (10 ml) maintained at -40 C. is added thereto from a dropping funnel. Thereafter, the mixture is slowly heated to 10 C. over 2 hours, and then 50 ml of a 10% aqueous solution of HCl at 0 C. is added thereto. The mixture is extracted with 100 ml of toluene. This extract is washed three times with 100 ml of purified water, and then is dried with sodium sulfate. Toluene is distilled off under reduced pressure, and 3.3 g of a residue is obtained. This residue is further washed with a mixed liquid of 100 ml of purified water and 100 ml of hexane, and thus 2.0 g of the compound V-a, which is 4-n-octylphenylboronic acid, is obtained. It is confirmed by 1H-NMR and IR that the compound is consistent with the intended product.
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