rac-(3S,4R)-4-bromo-3,4-dihydro-3-phenylisochromen-1-one

Base Information

• Chemical Name: rac-(3S,4R)-4-bromo-3,4-dihydro-3-phenylisochromen-1-one
• CAS No.: 78317-99-4
• Molecular Formula: C₁₅H₁₁BrO₂
• Molecular Weight: 303.155
• Mol file: 78317-99-4.mol

Synonyms:

Chemical Property of rac-(3S,4R)-4-bromo-3,4-dihydro-3-phenylisochromen-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of rac-(3S,4R)-4-bromo-3,4-dihydro-3-phenylisochromen-1-one

There total 8 articles about rac-(3S,4R)-4-bromo-3,4-dihydro-3-phenylisochromen-1-one 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: 99.0%

o-styrylbenzoic acid (60901-21-5,5079-90-3,66374-10-5) → rac-(3S,4R)-4-bromo-3,4-dihydro-3-phenylisochromen-1-one (78317-99-4,100954-48-1)

Guidance literature:

With N-Bromosuccinimide; trifluoroacetic acid; In acetonitrile; at 25 ℃; for 24h; Reagent/catalyst; Solvent; regioselective reaction;

DOI:10.1039/c6ob00756b

Reference yield:

o-styrylbenzoic acid (60901-21-5,5079-90-3,66374-10-5) → rac-(R)-3-[(S)-bromo(phenyl)methyl]isobenzofuran-1(3H)-one + rac-(3S,4R)-4-bromo-3,4-dihydro-3-phenylisochromen-1-one (78317-99-4,100954-48-1)

Guidance literature:

With N-Bromosuccinimide; In acetonitrile; at 25 ℃; for 24h; Reagent/catalyst; Solvent; Overall yield = 99 %Spectr.; regioselective reaction;

DOI:10.1039/c6ob00756b

Reference yield:

styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) → rac-(3S,4R)-4-bromo-3,4-dihydro-3-phenylisochromen-1-one (78317-99-4,100954-48-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: palladium diacetate; triphenylphosphine; triethylamine / 12 h / 100 °C

2.1: potassium hydroxide / water; ethanol / 12 h / 20 °C

3.1: (Z)-1-benzylcyclooct-1-ene / dichloromethane / 0.5 h / -30 °C

3.2: 6 h / -30 °C

With (Z)-1-benzylcyclooct-1-ene; palladium diacetate; triethylamine; triphenylphosphine; potassium hydroxide; In ethanol; dichloromethane; water;

DOI:10.1002/anie.201808320

upstream raw materials:

(Z)-2-(2-phenylethenyl)benzoic acid

(E)-2-styrylbenzoic acid

o-styrylbenzoic acid

styrene

Downstream raw materials:

erythro (3RS,8SR)-3-isobenzofuran-1(3H)-one

(RS)-3-((RS)-α-chloro-benzyl)-phthalide

2-(2-oxo-2-phenylethyl)benzoic acid

threo (3RS,8RS)-3-isobenzofuran-1(3H)-one

Refernces

• 1、 Nishiyori, Ryuichi,Tsuchihashi, Ayano,Mochizuki, Ayaka,Kaneko, Kazuma,Yamanaka, Masahiro,Shirakawa, Seiji. "Design of Chiral Bifunctional Dialkyl Sulfide Catalysts for Regio-, Diastereo-, and Enantioselective Bromolactonization". supporting information. p. 16747 - 16752. Retrieved 2018/11/01.
• 2、 Chen, Jie,Zhou, Ling,Tan, Chong Kiat,Yeung, Ying-Yeung. "An enantioselective approach toward 3,4-dihydroisocoumarin through the bromocyclization of styrene-type carboxylic acids". experimental part. p. 999 - 1009. Retrieved 2012/03/26.