bromoacetic acid 1-phenylbut-3-enyl ester

Base Information

• Chemical Name: bromoacetic acid 1-phenylbut-3-enyl ester
• CAS No.: 913723-00-9
• Molecular Formula: C₁₂H₁₃BrO₂
• Molecular Weight: 269.138
• Mol file: 913723-00-9.mol

Synonyms:

Chemical Property of bromoacetic acid 1-phenylbut-3-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of bromoacetic acid 1-phenylbut-3-enyl ester

There total 1 articles about bromoacetic acid 1-phenylbut-3-enyl ester 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:

(S)-1-Phenyl-3-buten-1-ol (77118-87-7,936-58-3) + 2-Bromoacetyl bromide (598-21-0) → bromoacetic acid 1-phenylbut-3-enyl ester (913723-00-9)

Guidance literature:

With pyridine; In dichloromethane; at 0 ℃;

DOI:10.1021/jo061296f

Reference yield:

bromoacetic acid 1-phenylbut-3-enyl ester (913723-00-9) → [(2-allyl-6-phenyltetrahydropyran-4-yl)oxy]triethylsilane (913723-06-5)

Guidance literature:

Multi-step reaction with 4 steps

1: OsO₄; NaIO₄ / dioxane; H₂O / 5 h / 20 °C

2: SmI₂ / CH₂Cl₂ / 2 h / 0 °C

3: diethyl ether; tetrahydrofuran / 2 h / -78 °C

4: 66 percent / TFA / CH₂Cl₂ / -78 - -40 °C

With sodium periodate; osmium(VIII) oxide; samarium diiodide; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; water;

DOI:10.1021/jo061296f

Reference yield:

bromoacetic acid 1-phenylbut-3-enyl ester (913723-00-9) → acetic acid (2S,4R,6S)-6-phenyl-4-triethylsilanyloxy-tetrahydro-pyran-2-yl ester

Guidance literature:

Multi-step reaction with 4 steps

1.1: OsO₄; NaIO₄ / dioxane; H₂O / 5 h / 20 °C

2.1: SmI₂ / CH₂Cl₂ / 2 h / 0 °C

3.1: 89 percent / triethylamine; DMAP / tetrahydrofuran / 6 h / 20 °C

4.1: diisobutylaluminum hydride / CH₂Cl₂ / 2.5 h / -78 °C

4.2: pyridine; DMAP / CH₂Cl₂ / 5 h / 0 - 25 °C

With dmap; sodium periodate; osmium(VIII) oxide; samarium diiodide; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water;

DOI:10.1021/jo061296f

upstream raw materials:

(S)-1-Phenyl-3-buten-1-ol

2-Bromoacetyl bromide

Downstream raw materials:

(4R,6S)-2-Allyl-6-phenyl-tetrahydro-pyran-2,4-diol

6-phenyl-4-triethylsilanyloxy-tetrahydro-pyran-2-one

[(2R,4S,6S)-6-phenyl-4-triethylsilanyloxy-tetrahydro-pyran-2-yl]acetaldehyde

[(2-allyl-6-phenyltetrahydropyran-4-yl)oxy]triethylsilane