171503-62-1

Upstream product

• 104-53-0 3-phenyl-propionaldehyde 
• 353-54-8 tribromofluoromethane 
• 929-05-5 1-ethoxybut-1-ene 
• 808128-25-8 (4-bromo-4-fluorobut-3-en-1-yl)benzene 
• 17655-74-2 β-ethoxystyrene 
• 171503-39-2 1,1-dibromo-1-fluoro-4-phenyl-2-butanol 
• 543-75-9 1,4-dioxene 
• 171503-49-4 1-(dibromofluoromethyl)-3-phenylpropyl p-toluenesulfonate 
• 109-92-2 ethyl vinyl ether 
• 171503-48-3 1-(dibromofluoromethyl)-3-phenylpropyl acetate 

Relevant academic research and scientific papers

Concise preparation of fluorine-containing carbocycles involving the Diels-Alder reaction using fluorinated alkene or diene derivatives

The Diels-Alder reaction of trifluorovinyl substances with various dienes proceeded well to give the corresponding trifluorinated cyclohexene derivatives in a regiospecific manner, while 2,3-difluorobuta-1,3-diene molecules also underwent a smooth Diels-A

Reactions of carbonyl compounds with phosphorus ylide generated from tribromofluoromethane and tris(dimethylamino)phosphine

The reactions of fluorinated ylide, generated from tris(dimethylamino) phosphine and tribromofluoromethane, with simple aldehydes and reactive ketones gave the expected Wittig reaction products. However, a ketone having a galactose skeleton afforded an acid fluoride, probably through an unprecedented CoreyChaykovski- type epoxide formation reaction, followed by spontaneous Meinwald rearrangement.

First stereospecific synthesis of (E)- or (Z)-α-fluoroenones via a kinetically controlled Negishi coupling reaction

A highly stereospecific synthesis of (E)- or (Z)-α-fluoro-α, β-unsaturated ketones 4, via a kinetically controlled Negishi palladium-catalyzed coupling reaction, was developed, providing an easy and general access to valuable fluorinated intermediates (pharmaceutical, peptide mimic, and so on). The synthesis involved a reaction between E/Z gem-bromofluoroolefins 2 and alkoxyvinylzinc species 6 under controlled reaction temperature. At 10 °C, (Z)-4 (70 to 99% yields) was obtained along with unreacted (Z)-2 (66 to 99% yields). At THF reflux, the recovered olefin was transformed into (E)-4 (up to 98% yield).

Efficient synthesis of fluoroalkenes via diethylzinc-promoted wittig reaction

The synthesis of α-fluoroacrylates and α-bromo-α- fluoroalkenes was achieved in very good yields using aldehydes and ketones, triphenylphosphine, diethylzinc as promoter, and ethyl dibromofluoroacetate or dibromofluoromethane, respectively. A change in th

A facile and mild method for the synthesis of terminal bromofluoroolefins via diethylzinc-promoted wittig reaction

Synthesis of 1-bromo-1-fluoroolefins was achieved in good yields via a Wittig reaction promoted by diethylzinc, even with nonactivated aldehydes and ketones as starting materials.

Generation and carbonyl addition reactions of dibromofluoromethyllithium derived from tribromofluoromethane as applied to the stereoselective synthesis of fluoro olefins and 2-bromo-2-fluoro-1,3-alkanediols

The treatment of tribromofluoromethane with BuLi in THF-Et2O (2: 1) at - 130°C generated dibromofluoromethyllithium, which was allowed to react smoothly with a coexisting aldehyde or ketone (RR'C=O) to give fluorinated alcohol RR'C(OH)CFBr2 (3) in good yield. Alcohol 3 was converted stereoselectively to (E)-1-bromo-1,2-difluoro olefin 5 via fluorination with Et2NSF3, followed by dehydrobromination with lithium 2,2,6,6- tetramethylpiperidide, while (E)-1-bromo-1-fluoro olefin was obtained with high selectivity by acetylation of 3, followed by reductive elimination using EtMgBr/(i-Pr)2NH. Difluoro olefin 5 underwent a cross-coupling reaction with an aryl, alkenyl, or alkynylmetal reagent to afford the corresponding fluoro olefin with retention of configuration. On the other hand, the treatment of RCH[OCH2O(CH2)2OCH3]CFBr2 with BuLi at -130°C in the presence of 4- heptanone gave the corresponding adduct diastereoselectively. The stereochemical outcome is explained in terms of chelation between lithium and oxygen atoms of the (2-methoxyethoxy)methyl group. Starting with 2- phenylpropanal, a product is obtained highly selectively containing three contiguous stereocenters including a -CFBr-moiety.

Stereoselective synthesis of (E)-ArCF=CFR and (E)-ArCH=CFR from ArCH(OH)CFBr2

(E)-vic-Difluoro olefin, RCF=CFBr, was synthesized by dehydrobromination of RCFHCFBr2 using lithium 2,2,6,6-tetramethylpiperidide. (E)-Fluoro olefin, RCH=CFBr, was obtained by treatment of RCH(OAc)CFBr2 with EtMgBr and HN(i-Pr)2.