tert-butyl 6-[(E/Z)-3-(3,5-dichloro-4-fluoro-phenyl)-4,4,4-trifluoro-but-2-enoyl]spiro[1H-isobenzofuran-3,3'-azetidine]-1'-carboxylate

Base Information

• Chemical Name: tert-butyl 6-[(E/Z)-3-(3,5-dichloro-4-fluoro-phenyl)-4,4,4-trifluoro-but-2-enoyl]spiro[1H-isobenzofuran-3,3'-azetidine]-1'-carboxylate
• CAS No.: 1398610-04-2
• Molecular Formula: C₂₅H₂₁Cl₂F₄NO₄
• Molecular Weight: 546.346
• Mol file: 1398610-04-2.mol

Synonyms:tert-butyl 6-[(E/Z)-3-(3,5-dichloro-4-fluoro-phenyl)-4,4,4-trifluoro-but-2-enoyl]spiro[1H-isobenzofuran-3,3'-azetidine]-1'-carboxylate

Chemical Property of tert-butyl 6-[(E/Z)-3-(3,5-dichloro-4-fluoro-phenyl)-4,4,4-trifluoro-but-2-enoyl]spiro[1H-isobenzofuran-3,3'-azetidine]-1'-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl 6-[(E/Z)-3-(3,5-dichloro-4-fluoro-phenyl)-4,4,4-trifluoro-but-2-enoyl]spiro[1H-isobenzofuran-3,3'-azetidine]-1'-carboxylate

There total 7 articles about tert-butyl 6-[(E/Z)-3-(3,5-dichloro-4-fluoro-phenyl)-4,4,4-trifluoro-but-2-enoyl]spiro[1H-isobenzofuran-3,3'-azetidine]-1'-carboxylate 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: 80.64%

1-(3,5-dichloro-4-fluorophenyl)-2,2,2-trifluoroethan-1-one (1190865-44-1) + tert-butyl 5'-acetyl-3'H-spiro[azetidine-3,1'-isobenzofuran]-1-carboxylate (1398609-81-8) → tert-butyl 6-[(E/Z)-3-(3,5-dichloro-4-fluoro-phenyl)-4,4,4-trifluoro-but-2-enoyl]spiro[1H-isobenzofuran-3,3'-azetidine]-1'-carboxylate (1398610-04-2)

Guidance literature:

With caesium carbonate; In toluene; at 110 ℃; for 16h;

Reference yield:

1-(4-chloro-3,5-difluorophenyl)-2,2,2-trifluoroethanone (1256467-08-9) + tert-butyl 5'-acetyl-3'H-spiro[azetidine-3,1'-isobenzofuran]-1-carboxylate (1398609-81-8) → tert-butyl 6-[(E/Z)-3-(3,5-dichloro-4-fluoro-phenyl)-4,4,4-trifluoro-but-2-enoyl]spiro[1H-isobenzofuran-3,3'-azetidine]-1'-carboxylate (1398610-04-2)

Guidance literature:

With caesium carbonate; In toluene; at 110 ℃; for 2h; Inert atmosphere; Dean-Stark;

Reference yield:

tert-butyl 6-bromospiro[1H-isobenzofuran-3,3‘-azetidine]-1‘-carboxylate (1398609-80-7) → tert-butyl 6-[(E/Z)-3-(3,5-dichloro-4-fluoro-phenyl)-4,4,4-trifluoro-but-2-enoyl]spiro[1H-isobenzofuran-3,3'-azetidine]-1'-carboxylate (1398610-04-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylamine; palladium diacetate; 1,3-bis-(diphenylphosphino)propane / ethanol / 0.08 h / 90 °C / Inert atmosphere

1.2: 4 h / 90 °C / Inert atmosphere

2.1: caesium carbonate / toluene / 2 h / 110 °C / Inert atmosphere; Dean-Stark

With 1,3-bis-(diphenylphosphino)propane; palladium diacetate; caesium carbonate; triethylamine; In ethanol; toluene;

upstream raw materials:

tert-butyl 6-bromospiro[1H-isobenzofuran-3,3‘-azetidine]-1‘-carboxylate

4-bromo-2-(chloromethyl)-1-iodobenzene

tert-butyl 3-oxoazetidine-1-carboxylate

1-(4-chloro-3,5-difluorophenyl)-2,2,2-trifluoroethanone

Downstream raw materials:

tert-butyl 5'-(3-(3,5-dichloro-4-fluorophenyl)-4,4,4-trifluoro-3-(nitromethyl)butanoyl)-3'H-spiro[azetidine-3,1'-isobenzofuran]-1-carboxylate

tert-butyl 5'-(3-(3,5-dichloro-4-fluorophenyl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl)-3'H-spiro[azetidine-3,1'-isobenzofuran]-1-carboxylate

5'-(3-(3,5-dichloro-4-fluorophenyl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl)-3'H-spiro[azetidine-3,1'-isobenzofuran] hydrochloride

1-(5'-(3-(3,5-dichloro-4-fluorophenyl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl)-3'H-spiro[azetidine-3,1'-isobenzofuran]-1-yl)-2-(methylsulfonyl)ethanone