3-Bromophenylboronic acid

white to light yellow crystal powder

500ml round bottom flask was placed 1-bromo-3-iodo-benzene (25.0g, 88mmol) was dissolved into 200ml of tetrahydrofuran. The reaction solution was cooled road -78 under a nitrogen atmosphere. A n-butyllithium (60.75ml, 97mmol) to the cooled solution was slowly added dropwise thereto for 30 minutes, the mixture was stirred for 1 hour at the same temperature. Trimethyl borate (11g, 106mmol) were added dropwise at the same temperature the mixture was stirred at room temperature overnight. It was acidified by dropwise addition of 2 normal hydrochloric acid to the reaction solution, which was stirred for 1 hour. Extraction with ethyl acetate was separated organic layer was concentrated under reduced pressure, crystallization was put in a cold n-hexane. Intermediate 11-a> was obtained. (12g, 67.6percent).Insert the 1-bromo-3-iodo-benzene (25.0g, 88mmol) in 500ml round bottom flask was put in a 200ml tetrahydrofuranDissolved.The reaction solution was cooled road -78 under a nitrogen atmosphere.It was slowly added dropwise for 30 minutes n-butyllithium (60.75ml, 97mmol) to the cooled solution, It was stirred for 1 hour at the same temperature.Trimethyl borate (11g, 106mmol) were added dropwise at the same temperature the mixture was stirred at room temperature overnight. It was acidified by dropwise addition of 2 normal hydrochloric acid to the reaction solution, which was stirred for 1 hour. Ethyl acetate was extracted with Tay organic layer was separated and concentrated under reduced pressure, crystallized into the cold n-hexane it was obtained (12g, 67.6percent).1, 3-dibromobenzene 25g(106 mnol) was added to purified ether (150 ml) and sufficiently stirred.The reaction is carried out at -75 ° C or below using a bath of liquid nitrogen / acetone. When the temperature of the reactor dropped to -75 or less, 50.8 ml (127 mmol) of 2.5M n-BuLi was added slowly, and the temperature was raised to room temperature. After 40 minutes of reaction, The temperature of the reaction was dropped below -75 , and then 46.4 g(318 mmol) was added and reacted for 12 hours to obtain a product. Add 300 ml of 2M HCl to distilled water and ice-filled beaker, stir the product several times, stirring well until all the ice is dissolved. The product is extracted with EA and water. In this case, use distilled water and wash thoroughly until it becomes neutral. The product is recrystallized using n-hexane to obtain the final purified product. 85percent yield.(105.9 mmol) of 1, 3-dibromobenzene in 500 ml of nitrogen at -78 ° C under N2 atmosphereTHF for 10 minutes, then, To this was slowly added dropwise 44 ml of 2.5 M n-BuLi through a dropping funnel, The resulting solution was stirred for 30 minutes.After that, 10.4 g (110 mmol) of trimethyl borate was slowly added dropwise thereto through a dropping funnel, then, The resulting solution was stirred at room temperature for 3 hours;Then, 300 ml of 1M hydrochloric acid solution was added thereto, and the extraction process was performed once. Then by usingThe organic layer separated from it was subjected to three extraction procedures with water and diethyl ether. And dried by using magnesium sulfateTo the organic layer, the residue obtained by evaporation of the solvent was isolated by silica gel column chromatography, To obtain 15.3 g (76.2 mmol, yield 71.9percent) of intermediate A-1.The experimental apparatus was thoroughly dried, and 35.4 g of 1, 3-dibromobenzene was added to a 2L three-necked flask.Add 700ml of dried tetrahydrofuran, After dissolution, the temperature was lowered to -78C, and 66 ml of 2.5M n-BuLi was added dropwise.After stirring for one hour at the temperature, 20.0 g of trimethyl borate was added dropwise at this temperature.After the addition was completed, the mixture was stirred at room temperature overnight.After the reaction is over, Add 4N hydrochloric acid solution, Extract with dichloromethane, The organic phase is washed to neutral with saturated saline solution.Dry, spin off the solvent, The crude product is boiled with ethyl acetate and filtered. The cake is the boric acid product.25g of intermediate G, The yield is 65percent.

suzuki reaction

Molecular Weight:200.83
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:199.96442
Monoisotopic Mass:199.96442
Topological Polar Surface Area:40.5
Heavy Atom Count:10
Complexity:110
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes