ChemicalBook CAS DataBase List 3-ETHOXY-4-METHOXYPHENYLBORONIC ACID

3-ETHOXY-4-METHOXYPHENYLBORONIC ACID synthesis

6synthesis methods

Product Name:3-ETHOXY-4-METHOXYPHENYLBORONIC ACID
CAS Number:915201-13-7
Molecular formula:C9H13BO4
Molecular Weight:196.01

5419-55-6
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$12.00/5g

52849-52-2 Synthesis

52849-52-2
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915201-13-7
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$71.00/250mg

Yield:915201-13-7 93%

Reaction Conditions:

Stage #1: 1-Bromo-3-ethoxy-4-methoxybenzenewith tert.-butyl lithium in tetrahydrofuran;pentane at -78; for 1 h;
Stage #2: Triisopropyl borate in tetrahydrofuran;pentane at -78 - 20; for 16 h;
Stage #3: with hydrogenchloride;water in tetrahydrofuran;pentane; for 0.166667 h;

Steps:

5.117.1

5.117.1 3-Ethoxy-4-Methoxyphenylboronic Acid A mixture of 4-Bromo-2-ethoxy-1-methoxybenzene (4.00 g, 17.3 mmol) in THF (75 mL) was cooled to -78° C.; during cooling, a precipitate formed. t-BuLi (22.4 mL, 1.7 M in pentane, 38.1 mmol) was added dropwise, while maintaining the temperature at -78° C. The mixture was stirred at -78° C. for 1 hour following completion of the addition. B(Oi-Pr)₃(9.76 g, 51.9 mmol) was added. The mixture was allowed to gradually warm to room temperature, and then stirred under nitrogen for 16 hours. 3N HCl (20 mL) was added, and the mixture stirred for 10 minutes. The mixture was poured into water (100 mL) and extracted with diethyl ether (3×75 mL), and the combined ethereal layers were washed with water (3×75 mL), dried (MgSO₄) and evaporated, providing 3.15 g of the product in 93% yield: ¹H NMR (DMSO-d₆) δ 1.32 (t, J=7.0 Hz, 3H), 3.75 (s, 3H), 3.99 (q, J=7.0 Hz, 2H), 6.90 (d, J=8.3 Hz, 1H), 7.35-7.37 (m, 2H).

References:

US2007/49618,2007,A1 Location in patent:Page/Page column 115