14088-71-2

Usage

Uses

Anthelmintic; antifungal.

InChI:InChI=1/C16H14Cl2O/c17-14-7-3-12(4-8-14)16(19,11-1-2-11)13-5-9-15(18)10-6-13/h3-11,19H,1-2H2

Upstream product

• 637-87-6 1-Chloro-4-iodobenzene 
• 6640-25-1 4-chlorophenyl cyclopropyl ketone 
• 23719-80-4 cyclopropylmagnesium bromide 
• 90-98-2 4,4'-Dichlorobenzophenone 
• 4606-07-9 ethyl cyclopropylcarboxylate 
• 873-77-8 (4-chlorphenyl)magnesium bromide 
• 4333-56-6 cyclopropyl bromide 

Downstream Products

• 856191-97-4 bromo-bis-(4-chloro-phenyl)-cyclopropyl-methane 
• 19685-60-0 bis-(4-chloro-phenyl)-cyclopropyl-methane 
• 86725-21-5 4,4′-(4-bromobut-1-ene-1,1-diyl)bis(chlorobenzene) 

Relevant academic research and scientific papers

Halogen-Lithium Exchange of Sensitive (Hetero)aromatic Halides under Barbier Conditions in a Continuous Flow Set-Up

A halogen-lithium exchange reaction of (hetero)aromatic halides performed in the presence of various electrophiles such as aldehydes, ketones, Weinreb amides, and imines using BuLi as exchange reagent and a commercially available flow set-up is reported. The organolithiums generated in situ were instantaneously trapped with various electrophiles (Barbier conditions) resulting in the formation of polyfunctional (hetero)arenes. This method enables the functionalization of (hetero)arenes containing highly sensitive functional groups such as esters, which are not tolerated in batch conditions.

A method for synthesis of homoallylic bromide

Cyclopropyl Grignard reagents react with carbonyl compounds in the presence of diethyl phosphite to give homoallylic bromides. The reaction is effectively carried out under mild conditions in a one-pot fashion with moderate to good yields.

Rapid access to halohydrofurans via bronsted acid-catalyzed hydroxylation/halocyclization of cyclopropyl methanols with water and electrophilic halides

A one-pot, two-step method to prepare 3-halohydrofurans efficiently by TfOH-catalyzed hydroxylation/halocyclization of cyclopropyl methanols with H2O and N-halosuccinimide (NXS, X=1, Br, Cl) or Selectfluor is described. The reactions proceed rapidly under mild and operationally straightforward conditions with a catalyst loading as low as 1 mol % and afford the 3-halohydrofuran products in moderate to excellent yields and, in most cases, with preferential cis diastereoselectivity. The method was shown to be applicable to cyclopropyl methanols containing electron-withdrawing, electron-donating, and sterically demanding functional groups and electrophilic halide sources. The mechanism is suggested to involve protonation of the alcohol substrate by the Bronsted acid catalyst and ionization of the starting material. This results in ring-opening of the cyclopropane moiety and in situ formation of a homoallylic alcohol intermediate, which undergoes subsequent intramolecular halocyclization on treating with the electrophilic halide source to give the halohydrofuran. The observed cis product selectivity is thought to be determined by the reaction proceeding through an in situ generated unsaturated alcohol intermediate that contains a (Z)-alkene moiety under the kinetically controlled conditions.