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ChemicalBook CAS DataBase List (4'-Propyl[1,1'-biphenyl]-4-yl)-boronic acid
153035-56-4

(4'-Propyl[1,1'-biphenyl]-4-yl)-boronic acid synthesis

5synthesis methods
61676-62-8 Synthesis
2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

61676-62-8
328 suppliers
$10.00/5g

58743-81-0 Synthesis
4-BROMO-4'-PROPYLBIPHENYL

58743-81-0
150 suppliers
$9.00/5g

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Yield: 80%

Reaction Conditions:

Stage #1:4-n-propyl-4'-bromobiphenyl in tetrahydrofuran at -78; for 1 h;
Stage #2:2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane in tetrahydrofuran at 20; for 1 h;

Steps:

2.1
[Experimental embodiment 2]: preparation of the compound in formula (I-4)Step 1: synthesize the compound in formula (2-A) (hereinafter “compound (2-A)”).First, 10 grams of 4-bromo-1-propyl benzene in formula (2) is placed in a two-neck bottle. The two-neck bottle is heated, and waterless THF is injected into the two-neck bottle. After the two-neck bottle is cooled to -78° C., 18 mL of an n-BuLi solution is slowly dripped into the two-neck bottle. After maintaining the reaction temperature at -78° C. for 1 hour, 10 mL of 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is slowly dripped into the two-neck bottle. After continuing the reaction for 1 hour, the bottle is heated to room temperature. 10 mL of distilled water is added to the above double-neck bottle, and low pressure evaporation-concentration is performed to remove the THF. Ethyl acetate and distilled water are used to extract the obtained mixture solution. Afterwards, the collected organic solution is desiccated by waterless magnesium sulfate, and the solid magnesium sulfate is removed by gravitational filtration. Then, low pressure evaporation-concentration is performed on the obtained mixture solution to remove the solvent. 9.47 grams of a white solid compound (2-A) is obtained. The yield is 80%.

References:

DAXIN MATERIALS CORPORATION US2012/264984, 2012, A1 Location in patent:Page/Page column 4-5