3-(Benzyloxy)-4-methoxyphenylboronic acid synthesis
- Product Name:3-(Benzyloxy)-4-methoxyphenylboronic acid
- CAS Number:243990-54-7
- Molecular formula:C14H15BO4
- Molecular Weight:258.08
121-43-7
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Yield: 80%
Reaction Conditions:
Stage #1:2-Benzyloxy-4-bromo-1-methoxybenzene with n-butyllithium in tetrahydrofuran;hexane at -78; for 1 h;Inert atmosphere;
Stage #2:Trimethyl borate in tetrahydrofuran;hexane at -78 - 20; for 5 h;Inert atmosphere;
Stage #3: with hydrogenchloride in tetrahydrofuran;hexane;water; pH=2 - 3 at -20 - 20;Inert atmosphere;
Steps:
6.1.4.3. 3-Benzyloxy-4-methoxyphenylboronic acid (42)
4-Bromo-3-methoxyphenol 25 (0.682 mmol, 0.200 g) was dissolved in freshly distilled THF (7 mL) in an oven-dried three-neck flask under argon.The temperature was cooled to 78 C and the solution was stirred for 30 min before dropwise addition of n-BuLi (1.6 N in hexanes,0.752 mmol, 0.470 mL). Once the addition of n-BuLi was completed, the mixture was stirred for another 30 min at 78 C beforethe dropwise addition of trimethyl borate (2.05 mmol, 0.233 mL).The reaction mixture was allowed to warm to room temperatureand stirred for 5 h. The temperature was cooled to 20 C andHCl 1 N was slowly added to reach pH = 2-3. The reaction mixture was allowed to warm to room temperature and extracted threetimes with EtOAc. The organic layers were combined, washed withbrine, dried with MgSO4 and concentrated in vacuo until precipitation occurred. Hexanes was then added to maximize precipitation.The solution was filtered and the solid was dried under vacuum.The precipitation/filtration procedure was repeated twice, giving42 as a white solid in an 80% yield (0.543 mmol, 0.140 g).mp = 135-155 C. 1H NMR (500 MHz, CDCl3): dH 7.80 (1H, d,J = 8.0), 7.70 (1H, s), 7.58-7.29 (6H, m), 7.04 (1H, d, J = 8.0), 5.28(2H, s), 3.99 (3H, s). 13C NMR (125 MHz, CDCl3): dC 153.6, 147.7,137.2, 130.3, 128.6, 127.9, 127.5, 120.5, 111.0, 71.3, 55.9. 11BNMR (160 MHz, CDCl3): dB 28.6. IR (ATR, ZnSe): mmax 1595, 1410,1319, 1250, 1216, 1179, 1133, 1018, 740, 710 cm1. HRMS (ESITOF,m/z): calcd for C14H14BO3 (M-H2O+H)+ = 241.1031, found 241.1049
References:
Cardinal, Sébastien;Paquet-Côté, Pierre-Alexandre;Azelmat, Jabrane;Bouchard, Corinne;Grenier, Daniel;Voyer, Normand [Bioorganic and Medicinal Chemistry,2017,vol. 25,# 7,p. 2043 - 2056]
78504-28-6
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243990-54-7
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100-39-0
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90-05-1
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613-70-7
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243990-54-7
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