The Case Studies
Access to Unique Molecular Structures (Suzuki-Coupling)
Low Temperature Synthesis of Boronic Acid and Palladium Catalyzed Coupling Reaction
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Access to Unique Molecular Structures (Suzuki-Coupling)
Low Temperature Synthesis of Boronic Acid and Palladium Catalyzed Coupling Reaction
Benefits with TMC by RohnerChem: Fast development, reliable and safe process, high quality.
Goal: To produce the 5-aryl-indole on multikilogramm scale.
- The challenge was the synthesis of the aryl boronic acid with an electrophilic group and the Suzuki coupling.
- The whole development including the production on pilot plant scale was carried out in less than 4 months.
- Both starting materials, 4-bromo-benzonitrile and 5-bromo-indole are standard products of RohnerChem.
- The lithiation of the bromo-benzonitrile was carried out at - 70 °C to avoid the attack of the BuLi on the nitrile group.
- The Suzuki coupling was carried out with 0.1 mol-% palladium catalyst.
- The palladium could be removed completely after the reaction (< 10 ppm).
Synthesis of Chiral Products
Asymmetric Hydrogenation under High Pressure
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Synthesis of Chiral Products
Asymmetric Hydrogenation under High Pressure
Benefit with TMC by RohnerChem: Access to sophisticated equipment, state of the art catalysis know how, fast development
The goal was the production of 400 kg of the chiral alcohol with an enantiomeric excess 98%.
The process was developed in collaboration with the technology provider Solvias. Solvias optimized the reaction
conditions and the catalyst. RohnerChem was responsible for scale-up and safety investigation as well as
the development of processing. Development and production of the 400 kg were successfully completed within two months.
The reaction was carried out at 25 °C and at 20 bar. The quality of the starting material and the handling of the homogeneous
catalyst were identified as the most critical factors.
Access to Special Benzoic Acid Derivatives
Carbonylation
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Access to Special Benzoic Acid Derivatives
Carbonylation
Benefit for Customer: Profound know how in carbonylation and access to facilities with CO handling capabilities.
The goal was the production of a several kilograms of an activated ester as an intermediate.
The palladium catalyzed carbonylation reaction was used for the synthesis of a sophisticated activated
succinimidyl ester. The process including optimization, processing and removal of the palladium was
developed within 2 months. The catalyst loading was optimized to a loading of s/c of 1000. The reaction
was run under moderate conditions: 5 bar, 120 °C.