ethyl 2-phenyl-3,3-difluoroacrylate

Base Information

• Chemical Name: ethyl 2-phenyl-3,3-difluoroacrylate
• CAS No.: 85278-32-6
• Molecular Formula: C₁₁H₁₀F₂O₂
• Molecular Weight: 212.196
• Mol file: 85278-32-6.mol

Synonyms:ethyl 2-phenyl-3,3-difluoroacrylate

Chemical Property of ethyl 2-phenyl-3,3-difluoroacrylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 2-phenyl-3,3-difluoroacrylate

There total 12 articles about ethyl 2-phenyl-3,3-difluoroacrylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 86.0%

ethyl 2-phenyldiazoacetate (22065-57-2) + difluoromethylene phosphobetaine → ethyl 2-phenyl-3,3-difluoroacrylate (85278-32-6)

Guidance literature:

With copper(I) bromide; In 1,4-dioxane; para-xylene; at 90 ℃; for 0.166667h; Reagent/catalyst; Time; Temperature; Schlenk technique; Inert atmosphere;

DOI:10.1021/acs.orglett.5b03159

Reference yield: 76.0%

ethyl 2-phenyldiazoacetate (22065-57-2) + [bromo(difluoro)methyl]-trimethyl-silane (115262-01-6) → C12H10F4O2 + ethyl 2-phenyl-3,3-difluoroacrylate (85278-32-6)

Guidance literature:

With tetrabutylammomium bromide; In 1,4-dioxane; at 80 ℃; for 12h; Solvent; Temperature; Reagent/catalyst; Catalytic behavior; Glovebox; Sealed tube; Inert atmosphere;

DOI:10.1021/jacs.5b09888

Reference yield: 74.0%

phenylglyoxylic acid ethyl ester (1603-79-8) + 2-((difluoromethyl)sulfonyl)pyridine (1219454-89-3) → ethyl 2-phenyl-3,3-difluoroacrylate (85278-32-6)

Guidance literature:

phenylglyoxylic acid ethyl ester; 2-((difluoromethyl)sulfonyl)pyridine; With tris(trimethylsilyl)amine; In N,N-dimethyl-formamide; toluene; at -60 - 20 ℃; for 1.08333h; Inert atmosphere; Schlenk technique;

With hydrogenchloride; In water; N,N-dimethyl-formamide; toluene; at -60 - 20 ℃; chemoselective reaction; Inert atmosphere; Schlenk technique;

DOI:10.1002/chem.201402183

upstream raw materials:

ethyl 2-(tert-butoxycarbonyl)-2-(bromodifluoromethyl)phenylacetate

t-butyl phenylacetate

ethyl 2-(tert-butoxycarbonyl)phenylacetate

Ethyl 2-phenylethanoate

Downstream raw materials:

2-((Z)-2-Chloro-3-phenyl-allyl)-isoindole-1,3-dione

(3,3-Difluoro-2-phenyl-allyl)-carbamic acid tert-butyl ester

1,1-difluoro-2-phenyl-3-phthalimidopropene

1,2-dibromo-1-fluoro-2-phenyl-3-phthalimidopropane

Refernces

• 1、 Li, Min,Wang, Yanhui,Tsui, Gavin Chit. "Palladium-Catalyzed Stereoselective C-F Bond Vinylation and Allylation of Tetrasubstituted gem-Difluoroalkenes via Stille Coupling: Synthesis of Monofluorinated 1,3- And 1,4-Dienes". supporting information. p. 8072 - 8076. Retrieved 2021/10/20.
• 2、 Tian, Panpan,Wang, Cheng-Qiang,Cai, Sai-Hu,Song, Shengjin,Ye, Lu,Feng, Chao,Loh, Teck-Peng. "F- Nucleophilic-Addition-Induced Allylic Alkylation". supporting information. p. 15869 - 15872. Retrieved 2016/12/23.