4'-METHOXYBIPHENYLBORONIC ACID synthesis
- Product Name:4'-METHOXYBIPHENYLBORONIC ACID
- CAS Number:156642-03-4
- Molecular formula:C13H13BO3
- Molecular Weight:228.05
121-43-7
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58743-83-2
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156642-03-4
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$61.00/1g
Yield: 58%
Reaction Conditions:
Stage #1:4-bromo-4'-methoxylbiphenyl with n-butyllithium in tetrahydrofuran;hexane at -78; for 1 h;Inert atmosphere;
Stage #2:Trimethyl borate in tetrahydrofuran;hexane at -78 - 5;
Steps:
18.B Step B:
Step B:
(4'-methoxy-[1,1'-biphenyl]-4-yl)boronic acid
To a solution of 4-bromo-4'-methoxy-1,1'-biphenyl (2 g, 7.63 mmol) in dry THF (30 mL) was added n-BuLi (9.2 ml, 22.9 mmol, 2.5 M in hexane) dropwise at -78° C. under N2 atmosphere. 1 hour later, (CH3O)3B (2.38 g, 22.9 mmol) was added dropwise at -78° C.
The resulting solution was stirred for 1 hour at -78° C. and overnight at 5° C.
After quenched with saturated NH4Cl solution, the mixture was extracted with EA (30 mL*2.) The combined organic layer was dried over anhydrous sodium sulfate.
The residue was purified by chromatography column to afford (4'-methoxy-[1,1'-biphenyl]-4-yl)boronic acid (1.0 g, 58% yield).
1H NMR (400 MHz, DMSO-d6): δ 8.06 (s, 2H), 7.84 (d, J=7.6 Hz, 2H), 7.63 (d, J=7.6 Hz, 2H), 7.58 (d, J=7.6 Hz, 2H), 7.02 (d, J=7.6 Hz, 2H), 3.80 (s, 3H).
References:
Arvinas, Inc.;Yale University;Crew, Andrew P.;Hornberger, Keith R.;Wang, Jing;Dong, Hanqing;Qian, Yimin;Crews, Craig M.;Jaime-Figueroa, Saul US2018/179183, 2018, A1 Location in patent:Paragraph 1608
58743-83-2
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$30.00/1g
156642-03-4
78 suppliers
$61.00/1g
29558-77-8
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156642-03-4
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5720-07-0
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156642-03-4
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106-37-6
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$9.00/5g
156642-03-4
78 suppliers
$61.00/1g