143026-79-3

Upstream product

• 31925-29-8 (2S,3R)-2-amino-3-hydroxy-3-(4-methylsulfonylphenyl)propionic acid ethyl ester 
• 100-68-5 methyl-phenyl-thioether 
• 90919-11-2 β-chloroethyl p-methylthiophenyl ketone 
• 701935-64-0 1-[4-(methylsulfanyl)phenyl]-2-propen-1-ol 
• 125872-62-0 (E)-3-[4-(methylsulfanyl)phenyl]prop-2-en-1-ol 
• 3446-89-7 4-(Methylthio)benzaldehyde 
• 1338046-00-6 (R)-((R)-3-benzyl-2-oxooxazolidin-4-yl)[4-(methylsulfonyl)phenyl]methyl acetate 

Downstream Products

• 73231-34-2 Florfenicol 

Relevant academic research and scientific papers

Synthesis method of florfenicol

The invention discloses a synthesis method of florfenicol, which comprises the following steps: by using (4R,5R)-2-dichloromethyl-4,5-dihydro-5-[4-(methylsulfonyl)phenyl]-4-oxazolemethanol (compound Ifor short) as a reaction raw material, carrying out chlorination, fluorination and hydrolysis to obtain florfenicol. The method has the advantages of cheap and easily available raw materials, simpleprocess operation, environmental protection and no pollution, accords with the industrialization concept of green production, and has extremely high industrialization value.

Method for continuously preparing florfenicol based on micro-reaction system

The invention provides a method for continuously preparing florfenicol based on a micro-reaction system. The preparation method comprises the following steps: respectively pumping an organic solution of a raw material {(4R, 5R)-2-(dichloromethyl)-5-[4-(methylsulfonyl) phenyl]-4, 5-dihydrooxazole-4-yl} methanol and an organic solution of a fluorinating reagent into a micro-mixer for mixing; introducing into a first micro-channel reactor for continuous fluorination reaction, and concentrating; obtaining a crude product; dissolving the crude product in alcohol and water, pumping into a second microchannel reactor, carrying out continuous hydrolysis ring-opening reaction, and separating and purifying a reaction product to obtain a florfenicol product. According to the method provided by the invention, the reaction time is only several minutes, the yield of the product florfenicol is greater than 95%, the operation is convenient, continuous and controllable, the amplification effect is avoided, the efficiency of the technological process is high, and the method has a very good industrial application prospect.

Catalytic Syn-Selective Nitroaldol Approach to Amphenicol Antibiotics: Evolution of a Unified Asymmetric Synthesis of (-)-Chloramphenicol, (-)-Azidamphenicol, (+)-Thiamphenicol, and (+)-Florfenicol

A unified strategy for an efficient and high diastereo- and enantioselective synthesis of (-)-chloramphenicol, (-)-azidamphenicol, (+)-thiamphenicol, and (+)-florfenicol based on a key catalytic syn-selective Henry reaction is reported. The stereochemistry of the ligand-enabled copper(II)-catalyzed aryl aldehyde Henry reaction of nitroethanol was first explored to forge a challenging syn-2-amino-1,3-diol structure unit with vicinal stereocenters with excellent stereocontrol. Multistep continuous flow manipulations were carried out to achieve the efficient asymmetric synthesis of this family of amphenicol antibiotics.

METHODS FOR PREPARING FLORFENIOL AND INTERMEDIATE THEREOF

The present invention discloses a method for preparing florfenicol and its intermediate (V), comprising an addition reaction, a ring closure reaction, a hydrolysis reaction, a ring opening reaction, a reduction reaction, a ring reaction, a fluorination reaction and a ring opening reaction. In the present method for preparing florfenicol, respective reaction steps can be continuously operated, therefore the methods of the present invention features simplified process and shorter synthetic route, and obtained florfenicol has high chiral purity and is of high yield. The method of the present invention for preparing florfenicol (TM) using the intermediate (V) avoids waste water pollution and reduces the cost for treating wastewater and alleviates environmental pollution. At the same time, the methods of the present invention eliminates a chiral resolution procedure, thus increasing the utilization rate of atoms in the reaction. As a result, cost is reduced and process is simplified.

Florfenicol intermediate state compound and method for preparing florfenicol intermediate

Shows-dihydro - 5-dihydro,5-(methylsulfonyl phenyl oxazoline) in the preparation good reagent to, obtain florfenicol intermediate by performing fluoro- reaction (4R,5R) - 2 - on-dichloro-methyl) - 4) 4-(methylsulfonyl ishikawa),intermediate compound, in, a microchannel reaction system to prepare a fluorobenzil intermediate, in a microchannel reactor ; The reaction container, is, prepared by the 130-160 °C, 1.6-2.0Mpa method of, the present invention. The method for preparing florfenicol intermediate, is shown in the present invention in a microchannel, reactor at a temperature of, ?0.0.0.60.0.60.0.60.60.0.60.60.60.60.60.60.60.60.60.60.60.60.6.

FLORFENICOL SYNTHESIZING METHOD

The present invention discloses a new florfenicol synthesizing method. The method synthesizes florfenicol products meeting requirements of the Drug Administration by a series of combinations of cyclization, selective reduction, fluorinated open ring, deprotection and acylation, hydroxyl sulfoacid esterified configuration converting reaction, hydrolysis reaction and the like. The synthesizing method of the present invention utilizing chiral amine closed-ring aziridine three-membered ring uses a physical separation method to repeatedly purify chiral aminoketone of high yield obtaining single R configuration, and uses selective reduction and converts the configuration to obtain florfenicol, greatly improving atom economy, while avoiding waste water pollution caused by the existing process, and greatly reducing costs for treating waste water and reducing pollution to the environment, thus lowering costs and simplifying the process. In addition, the present invention uses triethylamine hydrofluoride as a fluorinated open-ring reagent, to improve safety of a liquid reaction compared to a gas reaction and reduce corrosion of equipment, facilitating industrial production.

An efficient enantioselective synthesis of florfenicol via a vanadium-catalyzed asymmetric epoxidation

An efficient and highly enantioselective synthesis of florfenicol 1 was achieved with 37% overall yield starting from commercially available 4-methylthiobenzaldehyde. A key feature of the synthesis is the vanadium-catalyzed asymmetric epoxidation of allylic alcohol 5 with aq tert-butyl hydroperoxide to form (2S,3S)-epoxide 6.

PROCESS FOR PREPARING OXAZOLINE-PROTECTED AMINODIOL COMPOUNDS USEFUL AS INTERMEDIATES TO FLORFENICOL

Processes for preparing oxazoline compounds are disclosed. These oxazoline compounds are useful intermediates in the preparation of Florfenicol and related compounds.