(2R,3R)-1,1-bis(chloromethyl)-2,3-bis(3',5'-diphenylphenyl)cyclopropane

Base Information

• Chemical Name: (2R,3R)-1,1-bis(chloromethyl)-2,3-bis(3',5'-diphenylphenyl)cyclopropane
• CAS No.: 1268519-10-3
• Molecular Formula: C₄₁H₃₂Cl₂
• Molecular Weight: 595.611
• Mol file: 1268519-10-3.mol

Synonyms:(2R,3R)-1,1-bis(chloromethyl)-2,3-bis(3',5'-diphenylphenyl)cyclopropane

Chemical Property of (2R,3R)-1,1-bis(chloromethyl)-2,3-bis(3',5'-diphenylphenyl)cyclopropane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R)-1,1-bis(chloromethyl)-2,3-bis(3',5'-diphenylphenyl)cyclopropane

There total 12 articles about (2R,3R)-1,1-bis(chloromethyl)-2,3-bis(3',5'-diphenylphenyl)cyclopropane 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:

(2R,3R)-2,3-bis(3',5'-diphenylphenyl)cyclopropane-1,1-dimethanol (1268519-09-0) → (2R,3R)-1,1-bis(chloromethyl)-2,3-bis(3',5'-diphenylphenyl)cyclopropane (1268519-10-3)

Guidance literature:

With thionyl chloride; In N,N-dimethyl-formamide; at 0 ℃; for 24h; Reflux; Inert atmosphere;

DOI:10.1016/j.tetasy.2010.10.027

Reference yield:

3,5-dibromobenzaldehyde (56990-02-4) → (2R,3R)-1,1-bis(chloromethyl)-2,3-bis(3',5'-diphenylphenyl)cyclopropane (1268519-10-3)

Guidance literature:

Multi-step reaction with 8 steps

1.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere

2.1: methanesulfonamide; (9S,9"S)-9,9"-[phthalazine-1,4-diylbis-(oxy)]bis[10,11-dihydro-6'-methoxycinchonane] / tetrahydrofuran; water; tert-butyl alcohol / 120 h / 0 °C / Inert atmosphere

3.1: thionyl chloride / tetrachloromethane / 4 h / Inert atmosphere; Reflux

3.2: 3 h / 20 °C / Inert atmosphere

4.1: sodium hydride / 1,2-dimethoxyethane / 7 h / 20 °C / Inert atmosphere

5.1: sodium periodate; ruthenium trichloride / tetrachloromethane; water; acetonitrile / 24 h / 20 °C / Inert atmosphere

6.1: sodium tetrahydroborate; boron trifluoride diethyl etherate / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere

7.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / ethanol; water; toluene / 4 h / Reflux; Inert atmosphere

8.1: thionyl chloride / N,N-dimethyl-formamide / 24 h / 0 °C / Reflux; Inert atmosphere

With ruthenium trichloride; sodium tetrahydroborate; sodium periodate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; thionyl chloride; methanesulfonamide; boron trifluoride diethyl etherate; potassium tert-butylate; sodium hydride; potassium carbonate; (9S,9"S)-9,9"-[phthalazine-1,4-diylbis-(oxy)]bis[10,11-dihydro-6'-methoxycinchonane]; In tetrahydrofuran; tetrachloromethane; 1,2-dimethoxyethane; ethanol; water; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol; 1.1: Wittig reaction / 2.1: Sharpless dihydroxylation;

DOI:10.1016/j.tetasy.2010.10.027

Reference yield:

(1R,2R)-1,2-bis(3,5-dibromophenyl)ethane-1,2-diol (1268519-04-5) → (2R,3R)-1,1-bis(chloromethyl)-2,3-bis(3',5'-diphenylphenyl)cyclopropane (1268519-10-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: thionyl chloride / tetrachloromethane / 4 h / Inert atmosphere; Reflux

1.2: 3 h / 20 °C / Inert atmosphere

2.1: sodium hydride / 1,2-dimethoxyethane / 7 h / 20 °C / Inert atmosphere

3.1: sodium periodate; ruthenium trichloride / tetrachloromethane; water; acetonitrile / 24 h / 20 °C / Inert atmosphere

4.1: sodium tetrahydroborate; boron trifluoride diethyl etherate / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere

5.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / ethanol; water; toluene / 4 h / Reflux; Inert atmosphere

6.1: thionyl chloride / N,N-dimethyl-formamide / 24 h / 0 °C / Reflux; Inert atmosphere

With ruthenium trichloride; sodium tetrahydroborate; sodium periodate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; thionyl chloride; boron trifluoride diethyl etherate; sodium hydride; potassium carbonate; In tetrahydrofuran; tetrachloromethane; 1,2-dimethoxyethane; ethanol; water; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1016/j.tetasy.2010.10.027

upstream raw materials:

(1R,2R)-1,2-bis(3,5-dibromophenyl)ethane-1,2-diol

(4R,5R)-4,5-bis(3',5'-dibromophenyl)-(1,3,2)-dioxathiolane-2,2-dioxide

(2R,3R)-1-(ethoxycarbonyl)-2,3-bis(3',5'-dibromophenyl)cyclopropane-1-carboxylic acid

(2R,3R)-2,3-bis(3',5'-dibromophenyl)cyclopropane-1,1-dimethanol

Downstream raw materials:

(2R,3R)-1,1-bis[(diphenylphosphanyl)methyl]-2,3-bis(3',5'-diphenylphenyl)cyclopropane