4-N-HEXYLBENZENEBORONIC ACID

In a nitrogen atmosphere, an n-hexane solution of n-butyllithium (1.67 M, 131 mL, 218 mmol) was added dropwise to a solution in dry THF (300 mL) of 4-bromohexylbenzene (50.0 g, 207 mmol) at -75°C, and this mixture was stirred. After 2 hours, trimethoxyborane (64.6 g, 622 mmol) was added dropwise thereto. This mixture was stirred for further two hours. Thereafter, 1 N dilute hydrochloric acid (300 mL) was added dropwise thereto, and the resultant mixture was stirred for 30 minutes. This mixture was extracted with ethyl acetate, and the organic layer was washed with saturated aqueous sodium chloride solution, dried with sodium sulfate, and then concentrated under reduced pressure. Thus, intermediate 40 (42.5 g; yield, 99percent) was obtained as a colorless solid.In a nitrogen atmosphere, an n-hexane solution of n-butyllithium (1.67 M, 131 mL, 218 mmol) was added dropwise at −75° C. to a solution in dry THF (300 mL) of 4-bromohexylbenzene (50.0 g, 207 mmol), and the mixture was stirred. After 2 hours, trimethoxyborane (64.6 g, 622 mmol) was added dropwise thereto. This mixture was stirred for further 2 hours. Thereafter, 1-N diluted hydrochloric acid (300 mL) was added dropwise thereto, and this mixture was stirred for 30 minutes. The reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride solution, dried with sodium sulfate, and then concentrated under reduced pressure. Thus, intermediate 26 (42.5 g; yield, 99percent) was obtained as a colorless solid.The interior of the reaction vessel was repeatedly heated under reduced pressure and purged with nitrogen, The inside of the system was made a nitrogen atmosphere.12.06 g (0.05 mol) of p-Br omohexylbenzene was dissolved in 100 ml of dry THF and cooled to -78 ° C.To this was added dropwise 38 ml of Butyl litium (1.6 mol / l in Hexane)And reacted for 2 hours.To this was slowly added dropwise 2.86 g (0.05 mol) of Trimethyl boronic acid, and after 1 hour, the temperature was raised to room temperature.Water was added to this, neutralized with 1 N HCl, extraction was performed with ethyl acetate, Concentrated to give a white waxy crystal, 4-n-hexylphenylboronic acid6.98 g (yield 68percent) was obtained.

Molecular Weight:206.09
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:6
Exact Mass:206.1478100
Monoisotopic Mass:206.1478100
Topological Polar Surface Area:40.5
Heavy Atom Count:15
Complexity:154
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes