(-)-1-(3-bromo-1-hydroxy-2-propynyl)-3-phenoxybenzene

Base Information

• Chemical Name: (-)-1-(3-bromo-1-hydroxy-2-propynyl)-3-phenoxybenzene
• CAS No.: 1141933-01-8
• Molecular Formula: C₁₅H₁₁BrO₂
• Molecular Weight: 303.155
• Mol file: 1141933-01-8.mol

Synonyms:(-)-1-(3-bromo-1-hydroxy-2-propynyl)-3-phenoxybenzene

Chemical Property of (-)-1-(3-bromo-1-hydroxy-2-propynyl)-3-phenoxybenzene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-1-(3-bromo-1-hydroxy-2-propynyl)-3-phenoxybenzene

There total 2 articles about (-)-1-(3-bromo-1-hydroxy-2-propynyl)-3-phenoxybenzene 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:

C18H20O2Si (1141932-97-9) → (-)-1-(3-bromo-1-hydroxy-2-propynyl)-3-phenoxybenzene (1141933-01-8)

Guidance literature:

Multi-step reaction with 3 steps

1: dipyridinium dichromate / dichloromethane / 2 h / 20 °C / Molecular sieve

2: borane-THF; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran / 1.17 h / 0 °C

3: N-Bromosuccinimide; silver nitrate / acetone / 1.17 h / 20 °C / Darkness

With N-Bromosuccinimide; dipyridinium dichromate; borane-THF; silver nitrate; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; dichloromethane; acetone;

DOI:10.1016/j.bmc.2012.02.048

Reference yield:

3-Phenoxybenzaldehyde (39515-51-0) → (-)-1-(3-bromo-1-hydroxy-2-propynyl)-3-phenoxybenzene (1141933-01-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.25 h / -78 °C

1.2: 0.33 h / -78 - 20 °C

2.1: dipyridinium dichromate / dichloromethane / 2 h / 20 °C / Molecular sieve

3.1: borane-THF; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran / 1.17 h / 0 °C

4.1: N-Bromosuccinimide; silver nitrate / acetone / 1.17 h / 20 °C / Darkness

With N-Bromosuccinimide; dipyridinium dichromate; n-butyllithium; borane-THF; silver nitrate; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; hexane; dichloromethane; acetone;

DOI:10.1016/j.bmc.2012.02.048

Reference yield: 61.0%

2,2-dimethyl-3R-(2',2'-dibromovinyl)-cyclopropane-1R-carboxylic acid (53179-78-5,59952-39-5,61914-48-5,63538-10-3,63597-73-9,63949-77-9,72691-16-8,72691-18-0,74560-76-2) + (-)-1-(3-bromo-1-hydroxy-2-propynyl)-3-phenoxybenzene (1141933-01-8) → C23H19Br3O3 (1141933-07-4)

Guidance literature:

2,2-dimethyl-3R-(2',2'-dibromovinyl)-cyclopropane-1R-carboxylic acid; With 1,1'-carbonyldiimidazole; In dichloromethane; at 20 ℃; for 0.833333h;

(-)-1-(3-bromo-1-hydroxy-2-propynyl)-3-phenoxybenzene; With sodium hydride; In dichloromethane; for 0.5h;

DOI:10.1016/j.bmc.2012.02.048

upstream raw materials:

C₁₈H₂₀O₂Si

3-Phenoxybenzaldehyde

Downstream raw materials:

C₂₃H₁₉Br₃O₃