(R)-(4-(1-((tert-butyldimethylsilyl)oxy)propan-2-yl)-3-methylphenyl)boronic acid

Base Information

• Chemical Name: (R)-(4-(1-((tert-butyldimethylsilyl)oxy)propan-2-yl)-3-methylphenyl)boronic acid
• CAS No.: 1037082-19-1
• Molecular Formula: C₁₆H₂₉BO₃Si
• Molecular Weight: 308.301

Synonyms:(R)-(4-(1-((tert-butyldimethylsilyl)oxy)propan-2-yl)-3-methylphenyl)boronic acid

Chemical Property of (R)-(4-(1-((tert-butyldimethylsilyl)oxy)propan-2-yl)-3-methylphenyl)boronic acid

Chemical Property:

Purity/Quality:

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Technology Process of (R)-(4-(1-((tert-butyldimethylsilyl)oxy)propan-2-yl)-3-methylphenyl)boronic acid

There total 10 articles about (R)-(4-(1-((tert-butyldimethylsilyl)oxy)propan-2-yl)-3-methylphenyl)boronic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 66.0%

Trimethyl borate (121-43-7,63156-11-6) + (R)-(2-(4-bromo-2-methylphenyl)propoxy)(tert-butyl)dimethylsilane (1037082-18-0) → (R)-(4-(1-((tert-butyldimethylsilyl)oxy)propan-2-yl)-3-methylphenyl)boronic acid (1037082-19-1)

Guidance literature:

(R)-(2-(4-bromo-2-methylphenyl)propoxy)(tert-butyl)dimethylsilane; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.0833333h;

Trimethyl borate; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 14h;

DOI:10.1021/acs.jmedchem.6b00244

Reference yield:

1-allyl-4-bromo-2-methylbenzene (1037088-26-8) → (R)-(4-(1-((tert-butyldimethylsilyl)oxy)propan-2-yl)-3-methylphenyl)boronic acid (1037082-19-1)

Guidance literature:

Multi-step reaction with 8 steps

1.1: rhodium(III) chloride hydrate; sodium periodate / water; acetonitrile; tetrachloromethane / 2.5 h / 20 °C

2.1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 2 h / 20 °C

3.1: n-butyllithium / tetrahydrofuran; hexane / 0.08 h / -78 °C

3.2: 1 h / -78 °C

4.1: sodium hexamethyldisilazane / tetrahydrofuran / 1.08 h / -78 °C

4.2: 5.5 h / -78 - 20 °C

5.1: lithium hydroperoxide / tetrahydrofuran; water / 1 h / 0 °C

6.1: borane-THF / tetrahydrofuran / 65 h / 0 - 20 °C

7.1: 1H-imidazole / dichloromethane / 3 h / 20 °C

8.1: n-butyllithium / tetrahydrofuran; hexane / 0.08 h / -78 °C

8.2: 14 h / -78 - 20 °C

With 1H-imidazole; sodium periodate; n-butyllithium; borane-THF; oxalyl dichloride; lithium hydroperoxide; rhodium(III) chloride hydrate; sodium hexamethyldisilazane; In tetrahydrofuran; tetrachloromethane; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/acs.jmedchem.6b00244

Reference yield:

2-(4-bromo-2-methyl-phenyl)acetic acid (853796-39-1) → (R)-(4-(1-((tert-butyldimethylsilyl)oxy)propan-2-yl)-3-methylphenyl)boronic acid (1037082-19-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 2 h / 20 °C

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.08 h / -78 °C

2.2: 1 h / -78 °C

3.1: sodium hexamethyldisilazane / tetrahydrofuran / 1.08 h / -78 °C

3.2: 5.5 h / -78 - 20 °C

4.1: lithium hydroperoxide / tetrahydrofuran; water / 1 h / 0 °C

5.1: borane-THF / tetrahydrofuran / 65 h / 0 - 20 °C

6.1: 1H-imidazole / dichloromethane / 3 h / 20 °C

7.1: n-butyllithium / tetrahydrofuran; hexane / 0.08 h / -78 °C

7.2: 14 h / -78 - 20 °C

With 1H-imidazole; n-butyllithium; borane-THF; oxalyl dichloride; lithium hydroperoxide; sodium hexamethyldisilazane; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/acs.jmedchem.6b00244

upstream raw materials:

Trimethyl borate

(R)-(2-(4-bromo-2-methylphenyl)propoxy)(tert-butyl)dimethylsilane

1-allyl-4-bromo-2-methylbenzene

2-(4-bromo-2-methyl-phenyl)acetic acid

Downstream raw materials:

C₂₁H₂₂N₂O₄

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