4,4,5,5-tetramethyl-2-[1-methyl-4-(2-methyl-[1,3]dioxolan-2-yl)-1-phenylsulfanyl-butyl]-[1,3,2]dioxaborolane

Base Information

• Chemical Name: 4,4,5,5-tetramethyl-2-[1-methyl-4-(2-methyl-[1,3]dioxolan-2-yl)-1-phenylsulfanyl-butyl]-[1,3,2]dioxaborolane
• CAS No.: 66080-33-9
• Molecular Formula: C₂₁H₃₃BO₄S
• Molecular Weight: 392.368

Synonyms:4,4,5,5-tetramethyl-2-[1-methyl-4-(2-methyl-[1,3]dioxolan-2-yl)-1-phenylsulfanyl-butyl]-[1,3,2]dioxaborolane

Chemical Property of 4,4,5,5-tetramethyl-2-[1-methyl-4-(2-methyl-[1,3]dioxolan-2-yl)-1-phenylsulfanyl-butyl]-[1,3,2]dioxaborolane

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Technology Process of 4,4,5,5-tetramethyl-2-[1-methyl-4-(2-methyl-[1,3]dioxolan-2-yl)-1-phenylsulfanyl-butyl]-[1,3,2]dioxaborolane

There total 4 articles about 4,4,5,5-tetramethyl-2-[1-methyl-4-(2-methyl-[1,3]dioxolan-2-yl)-1-phenylsulfanyl-butyl]-[1,3,2]dioxaborolane 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: 71.0%

1-chloro-4-(1,3-dioxolane)-n-pentane (5978-08-5) + pinacol 1-(phenylthio)ethane-1-boronate (66080-24-8) → 4,4,5,5-tetramethyl-2-[1-methyl-4-(2-methyl-[1,3]dioxolan-2-yl)-1-phenylsulfanyl-butyl]-[1,3,2]dioxaborolane (66080-33-9)

Guidance literature:

With n-butyllithium; diisopropylamine; In tetrahydrofuran; under Ar or N2, first BuLi was added to diisopropylamine in THF with stirring at 0°C, then addn. of B compd., stirring for 12 h at 0°C, addn. of alkyl halide, mixt. kept for 2-4 h at room temp.; addn. of aq. 10 % phosphoric acid, extd. with ether, distd. elem.anal.,yield only 48 % after 3 h;

Reference yield:

2,3-dimethyl-2,3-butane diol (76-09-5) → 4,4,5,5-tetramethyl-2-[1-methyl-4-(2-methyl-[1,3]dioxolan-2-yl)-1-phenylsulfanyl-butyl]-[1,3,2]dioxaborolane (66080-33-9)

Guidance literature:

Multi-step reaction with 3 steps

1: diethyl ether

2: (i) LDA, THF, (ii) /BRN= 969135/

3: (i) LDA, TMEDA, THF, (ii) /BRN= 104617/

In diethyl ether;

DOI:10.1021/ja00472a066

Reference yield:

(phenylthio)methaneboronic acid (67975-88-6) → 4,4,5,5-tetramethyl-2-[1-methyl-4-(2-methyl-[1,3]dioxolan-2-yl)-1-phenylsulfanyl-butyl]-[1,3,2]dioxaborolane (66080-33-9)

Guidance literature:

Multi-step reaction with 3 steps

1: diethyl ether

2: (i) LDA, THF, (ii) /BRN= 969135/

3: (i) LDA, TMEDA, THF, (ii) /BRN= 104617/

In diethyl ether;

DOI:10.1021/ja00472a066

upstream raw materials:

1-chloro-4-(1,3-dioxolane)-n-pentane

pinacol 1-(phenylthio)ethane-1-boronate

2,3-dimethyl-2,3-butane diol

4,4,5,5-tetramethyl-2-((phenylsulfanyl)methyl)-1,3,2-dioxaborolane

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