91348-52-6

Upstream product

• 23755-73-9 triethyl bromophosphonoacetate 
• 555-16-8 4-nitrobenzaldehdye 
• 124755-24-4 ethyl [bis(2,2,2-trifluoroethoxy)phosphinyl]acetate 
• 803-14-5 ethyl 2-bromo-2-(triphenylphosphoranylidene)acetate 
• 599-99-5 ethyl tribromoacetate 
• 64-17-5 ethanol 
• 124520-68-9 α-bromo-4-nitro-cinnamic acid 

Downstream Products

• 35283-08-0 ethyl 3-(4-nitrophenyl)prop-2-ynoate 
• 1039341-10-0 (Z)-ethyl 3-(1,3-dioxoisoindolin-2-yl)-3-(4-nitrophenyl)acrylate 
• 42393-45-3 (Z)-2-bromo-3-(4-nitro-phenyl)-acrylic acid 

Relevant academic research and scientific papers

Preparation of α-bromoacrylates: One-pot procedure for the synthesis of conjugated acetylenic carboxylates from aldehydes with Ph3P/ Br3CCO2Et

We have established the optimal conditions for the Wittig reaction for synthesizing α-bromoacrylates with a high selectivity, and developed a simple and efficient one-pot procedure for preparing various conjugated acetylenic carboxylates in moderate to high yields. Georg Thieme Verlag Stuttgart.

A convenient synthesis and the asymmetric hydrogenation of N-phthaloyl dehydroamino acid esters

(Chemical Equation Presented) A convenient synthetic method was reported for the preparation of N-phthaloyl dehydroamino acid esters from easily accessible vinyl bromides (or vinyl tosylate) and potassium phthalimide. Rh-catalyzed asymmetric hydrogenation

Site-specific preparation of 2-carboalkoxy-4-substituted naphthalenes and 9-alkylphenanthrenes and evidence for an allene intermediate in the novel base-catalyzed cyclization of 2-alkynylbiphenyls

A site-specific preparation of 2-carboalkoxy-4-substituted naphthalenes and 9-alkylphenanthrenes is described. The successful cyclization of an allene intermediate provides supportive evidence for the previously proposed mechanism.

Microwave-assisted tandem nucleophilic substitution-Wittig reaction of α-hypervalent iodine functionalized phosphonium ylide

Under microwave irradiation conditions the tandem nucleophilic substitution-Wittig reaction of α-hypervalent iodine functionalized phosphonium ylide can occur readily to afford α-heteroatom substituted-α,β-unsaturated enoates in good yields stereo-selecti

α-hypervalent iodine functionalized phosphonium and arsonium ylides and their tandem reaction as umpolung reagents

α-Hypervalent iodine functionalized phosphonium and arsonium ylides 2 can be used as umpolung ylides to react with nucleophiles to give α-heteroatom substituted ylides 4 in good yields. The nucleophilic substitution - Wittig tandem reaction of 2 can occur smoothly to provide an efficient method for the synthesis of (Z)-α-halo-α,β-unsaturated enoates or enones 6, stereoselectively.

A one-pot synthesis of (E)-α-bromo-α,β-unsaturated esters and their trifluoromethylation: A general and stereoselective route to (E)-α-trifluoromethyl-α,β-unsaturated esters

Bromination of a phosphonate anion derived in situ from ethyl bis(2,2,2-trifluoroethyl)phosphonoacetate 3 followed by the addition of aldehydes produced (E)-α-bromo-α,β-unsaturated esters 5 stereoselectively. The treatment of 5 with FSO2CF2CO2Me and CuI in DMF/HMPA provided (E)-α-trifluoromethyl-α,β-unsaturated esters 6.

High-pressure induced domino-Horner-Wadsworth-Emmons (HWE) -Michael reactions

A new protocol for the alkenylation of carbonyl compounds with phosphonates (Horner-Wadsworth-Emmons reaction) is described. Aldehydes react with phosphonates already at room temperature in the presence of triethylamine without further activation by Lewis-acids if high-pressure (8 kbar) is applied to the system. Based on this protocol a domino process was developed combining the HWE reaction with a Michael reaction, thus allowing the one-pot synthesis of β-amino esters, β-thio esters or β-thio nitriles.

Synthesis of 2′,3′-Dideoxy-2′-trifluoromethylnucleosides from α-Trifluoromethyl-α,β-unsaturated Ester

The treatment of α-bromo-α,β-unsaturated esters 2 with FSO2CF2CO2Me and CuI in DMF/HMPA constitutes a new synthetic scheme for the preparation of α-trifluoromethyl-α,β-unsaturated esters 3. The trifluoromethylation of (Z)/(E)-ethyl 3-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-bromo-2-propenoate (2e), which is derived from 1-(R)-glyceraldehyde acetonide, yields the key intermediate α-trifluoromethyl-αβ-unsaturated esters 3e. This is transformed into anomeric acetates 8a and 8b and is used for the synthesis of a number of 2′,3′-dideoxy-2′-trifluoromethylnucleosides.

A new route to α-trifluoromethyl-α,β-unsaturated esters

The treatment of α-bromo-α,β-unsaturated esters with FSO2CF2CO2Me and CuI in DMF/HMPA constitutes a new synthetic scheme for the preparation of α-trifluoromethyl-α,β-unsaturated esters. (C) 2000 Elsevier Science Ltd.