ChemicalBook CAS DataBase List 4-(4'-PROPOXYPHENYL)PHENYLBORONIC ACID

4-(4'-PROPOXYPHENYL)PHENYLBORONIC ACID synthesis

5synthesis methods

Product Name:4-(4'-PROPOXYPHENYL)PHENYLBORONIC ACID
CAS Number:849062-20-0
Molecular formula:C15H17BO3
Molecular Weight:256.1

154020-02-7 Synthesis

154020-02-7
20 suppliers
$55.00/250mg

849062-20-0
36 suppliers
$60.00/100mg

Yield:849062-20-0 98.4%

Reaction Conditions:

Stage #1: 4-bromo-4'-n-propoxybiphenylwith n-butyllithium in tert-butyl methyl ether at -20; for 2 h;Inert atmosphere;
Stage #2: with Triisopropyl borate in tetrahydrofuran;tert-butyl methyl ether at -60 - 20;
Stage #3: with hydrogenchloride;water in tetrahydrofuran;tert-butyl methyl ether at 20; for 0.166667 h;

Steps:

General procedure: n-BuLi (2.5 M, 7.4 mL, 18 mmol) was added dropwise to a solution of compound 14c (4.5 g, 13 mmol) in MTBE (50 mL) at -20 °C under nitrogen atmosphere. After stirring for 2 h, the reaction mixture was cooled to -60 °C and was added THF (6 mL). Then, a solution of (i-PrO)₃B (6.1 mL, 26 mmol) in MTBE (8 mL) was added dropwise to the resulting mixture and was stirred for 1 h. The reaction mixture was allowed to warm to room temperature, stirred overnight and treated with 2 M HCl (50 mL) for 10 min. The organic layer was separated and the solvent was evaporated under reduced pressure. The residue was added hexane (40 mL) and stirred for 10 min. After filtration, the filter cake was washed by hexane-MTBE (8: 1) to give 15c (3.7 g, yield 91.4%) as white solid.

References:

Yao, Jianzhong;Liu, Hongming;Zhou, Ting;Chen, Hai;Miao, Zhenyuan;Sheng, Chunquan;Zhang, Wannian [European Journal of Medicinal Chemistry,2012,vol. 50,p. 196 - 208] Location in patent:supporting information; experimental part

29558-77-8 Synthesis