18775-64-9

Upstream product

• 4850-49-1 1-phenyl-1,3-propanediol 
• 123-91-1 1,4-dioxane 
• 7647-01-0 hydrogenchloride 
• 4436-23-1 2-phenyloxetane 
• 100-42-5 styrene 
• 75-09-2 dichloromethane 
• 10534-59-5 tetrabutylammonium acetate 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 614-27-7 methyl 3-oxo-3-phenylpropionate 
• 7719-09-7 thionyl chloride 
• 772-00-9 4-phenyl-1,3-dioxane 
• 628-51-3 diacetoxymethane 

Downstream Products

• 772-00-9 4-phenyl-1,3-dioxane 
• 33994-17-1 (3-bromo-1-chloropropyl)benzene 
• 219745-27-4 4-{2-[4-(3-Bromo-1-phenyl-propoxy)-phenylcarbamoyl]-phenoxy}-butyric acid ethyl ester 

Relevant academic research and scientific papers

Kinetic resolution of primary alcohols having remote stereogenic centers: lipase mediated kinetic resolution of (±)-3-chloro-3-arylpropanols

Kinetic resolutions of (±)-3-chloro-3-arylpropanols by lipase mediated acetylation are described for the first time. Acetylation with CCL provided the best enantioselectivity amongst the enzymes used. Enantiomerically enriched products were obtained with up to 78% ee after two successive lipase-catalyzed acetylations. Different substituents on the aromatic ring and bromide, instead of chloride, on the substrates were found to have no drastic influence on the enantioselectivity of the reaction.

Selective monochlorination of unsymmetrical vicinal diols with chlorinated iminium chlorides

Chlorinated iminium chlorides have been identified to promote the highly efficient and selective mono-chlorination of unsymmetrical vicinal diols. Vilsmeier reagent, namely, (chloromethylene)dimethyliminium chloride, enables highly reactive and regioselective chlorination of 1,2- and 1,3-diols featured one secondary benzylic hydroxy group and one primary aliphatic hydroxy group to give the corresponding 1,2- and 1,3-chlorohydrins. Viehe's salts (α,α-dichloro iminium salts) exhibit excellent reactivity and good selectivity for vicinal diols to give the corresponding chlorohydrin carbamates via a cyclic intermediate in situ. The chlorination protocols tolerate diverse functional groups, including halogens, naphthalene rings, nitro, and cyano. Moreover, the optical purity of chiral diols could be retained during this chlorination reaction.

Silver-Catalyzed C(sp3)-H Chlorination

A silver-catalyzed chlorination of benzylic, tertiary, and secondary C(sp3)-H bonds was developed. The reaction proceeded with as low as 0.2 mol % catalyst loading at room temperature under air atmosphere with synthetically useful functional group compatibility. The regioselectivity and reactivity tendencies suggest that the chlorination proceeded through a radical pathway, but an intermediate alkylsilver species cannot be ruled out.

Regioselective monochloro substitution in carbohydrates and non-sugar alcohols via Mitsunobu reaction: Applications in the synthesis of reboxetine

A regioselective high yielding monochloro substitution (chlorohydrin formation) via Mitsunobu reaction is reported. In carbohydrates and sterically hindered non-sugars, only the primary hydroxyl group is chlorinated, whereas in the non-sugar 1,2- and 1,3-alcohols, predominantly the secondary chloride substitution occurs. The versatile methodology provides indirect access to epoxides with the retention of configuration, as against conventional Mitsunobu reaction which generates epoxides with inversion. The methodology was successfully used as a key step in the synthesis of optically active diastereoisomers of the antidepressant drug reboxetine from (R)-2,3-O- cyclohexylidene-d-glyceraldehyde in ～43% overall yields. The Royal Society of Chemistry.

Boron trifluoride mediated prins reaction of methylene diacetate with styrenes. One-pot synthesis of 3-chloro-3-arylpropanols

A one-pot procedure was developed for the synthesis of 3-chloro-3- arylpropanols, which are important starting materials for the synthesis of biologically active benzanilide derivatives. Styrenes were reacted with methylene diacetate in the presence of boron trifluoride to give the corresponding 3-chloro-3-arylpropanols in 36-84% yield by the Prins reaction. A strongly electron-donating methoxy substituent at either the ortho or para position of the styrene did not give the expected 3-chloro-3-arylpropanols due to polymerization. Styrene with a strongly electron-withdrawing nitro substituent gave the corresponding 3-chloro-3-arylpropanol in very low yield. Under the same reaction conditions, substituted norbornene gave a tricyclic ether. A very easy procedure for the synthesis of methylene diacetate is also reported. Georg Thieme Verlag Stuttgart.

Synthesis of benzanilide derivatives as dual acting agents with α1- adrenoceptor antagonistic action and steroid 5-α reductase inhibitory activity

Synthesis of benzanilide derivatives which have dual α1-adrenoceptor antagonistic action and steroid 5α-reductase inhibitory activity and their structure-activity relationships is described.