88920-84-7

Upstream product

• 88920-82-5 1,1-Dichloro-4-phenyl-1-trimethylsilanyl-butan-2-ol 
• 2233-00-3 3,3,3-trichloro-1-propene 
• 108-88-3 toluene 
• 124-19-6 nonan-1-al 
• 358720-79-3 acetic acid 3-phenyl-1-trichloromethyl-propyl ester 
• 358720-84-0 trimethyl(1,1,1-trichloro-4-phenylbutan-2-yloxy)silane 
• 104-53-0 3-phenyl-propionaldehyde 
• 56-23-5 tetrachloromethane 
• 650-51-1 sodium trichloroacetate 
• 82772-38-1 α-(trichloromethyl)benzenepropanol 
• 75-62-7 Bromotrichloromethane 
• 119405-97-9 4-phenyl-1,1-dibromo-1-butene 

Downstream Products

• 103240-58-0 2,6-diphenylhexa-2,3-diene 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 76181-40-3 1-chloro-3,4-dihydronaphthalene 
• 16520-62-0 4-Phenyl-1-butyne 

Relevant academic research and scientific papers

A Robust One-Step Approach to Ynamides

A robust one-step synthetic strategy for ynamide with cheap and easily available stock chemicals vinyl dichlorides and electron deficient amides as the starting material is described. In the absence of transition-metal catalyst, the reaction proceeds under mild reaction conditions in open air and thus rendering a convenient operation. This strategy is not only suitable for both terminal and internal ynamide synthesis but also amenable for large-scale preparation. Broad substrate scopes with respect to vinyl dichloride as well as electron-deficient amide were observed.

Development of a general copper-catalyzed vinylic Finkelstein reaction—application to the synthesis of the C1–C9 fragment of laingolide B

An efficient and broadly applicable procedure for the copper-catalyzed vinylic Finkelstein reaction is reported. Using a simple, readily available and cheap catalytic system, a broad range of alkenyl iodides and bromides can be smoothly converted to their lower homologues with high yields and full retention of the double bond geometry. Key features of this vinylic Finkelstein reaction are its broad applicability, enabling the conversion of readily available alkenyl iodides to their less available brominated and chlorinated counterparts, and the mild reaction conditions compatible with a range of highly functionalized substrates. The potential of this vinylic halogen exchange reaction in total synthesis and medicinal chemistry was demonstrated by its successful use for the synthesis of the C1–C9 fragment of laingolide B and for the late-stage modification of drug-like molecules. The extension of this halogen exchange to the acetylenic and allenic Finkelstein reactions is also reported.

The use of bromotrichloromethane in chlorination reactions

Carbon tetrachloride is no longer used as a common solvent due to its toxicity and harmful environmental impact. The synthesis of gem-dichloroalkenes from aldehydes by using triphenylphosphine typically requires carbon tetrachloride as a solvent. We report that stoichiometric bromotrichloromethane in acetonitrile can be used in place of solvent quantities of carbon tetrachloride in this transformation. Similarly, bromotrichloromethane in dichloromethane can be used for the room-temperature Appel reaction of benzyl alcohols to form benzyl chlorides, which is commonly carried out in refluxing carbon tetrachloride. Georg Thieme Verlag Stuttgart New York.

Activation of 1,1-difluoro-1-alkenes with a transition-metal complex: Palladium(II)-catalyzed friedel - crafts-type cyclization of 4,4-(difluorohomoallyl)arenes

(Chemical Equation Presented) Cationic palladium(II) ([Pd(MeCN) 4](BF4)2) provides the first transition-metal-catalyzed method for electrophilic activation of electron-deficient 1,1-difluoro-1-alkenes, which allows their Friedel-Crafts-type cyclization with an intramolecular aryl group via a Wacker-type process. By using BF3·OEt2, the cyclization was effected by a catalytic amount of the palladium without its reoxidation.

Novel ambiphilic dichlorocarbenoid equivalent in alkene cyclopropanation and carbonyl olefination

The Ti-Mg-dichloromethylene complexes derived from the oxidative addition of CCl4 to the Mg-TiCl4 bimetallic species serve as a novel class of ambiphilic dichlorocarbenoid equivalents. Not only is Ti-Mg-dichlorocarbenoid highly selective but also it seems highly reactive in both alkene cyclopropanations and carbonyl dichloromethylenations.

Process for the preparation of cyclopropylacetylene

The present invention relates generally to novel methods for the preparation of cyclopropylacetylene which is an essential reagent in the asymmetric synthesis of (S)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-benzoxazin-2-one; a useful human immunodeficiency virus (HIV) reverse transcriptase inhibitor with superior anti-retroviral activity. In the process, for example, cyclopropane carboxaldehyde is alkylated to form 1,1,1-trichloro-2-cyclopropyl-ethanol; which in turn undergoes elimination to form 1,1-dichloro-2-cyclopropyl-ethene; which in turn undergoes elimination to form cyclopropyl acetylene.

Reactions of coordinated geminal dichromium reagents with aldehydes: Stereoselective formation of (Z)-2-chloroalk-2-en-1-ols

Treatment of a carbonate ester of 2,2,2-trichloroethanol derivative with CrCl2-DMF in THF gives a β-carbonate-coordinated geminal dichromium species, which adds to an aldehyde and eliminates an acyloxychromium group to afford a (Z)-2-chloroalk-

A new and practical synthesis of vinyl dichlorides via a non-Wittig-type approach

A practical approach for the conversion of aldehydes to vinyl dichlorides has been developed. These are three-step, one-pot reactions involving the formation of trichlorocarbinol by treatment of aldehydes with trichloroacetic acid and sodium trichloroacetate followed by in situ protection and elimination reactions to form the desired vinyl dichlorides in 85 to 95% yields. (C) 2000 Dupont Pharmaceuticals Company.

A CONVENIENT AND NOVEL SYNTHESIS OF 1,1-DICHLOROALKENES USING α-LITHIATED DICHLOROMETHYLTRIMETHYLSILANE AND ALDEHYDES

Various 1,1-dichloroalkenes can be prepared by the reaction of α-lithiated dichloromethyltrimethylsilane with aldehydes followed by hydrolysis.