3-[(1S)-1-(4-bromo-phenyl)-but-3-enyloxy]-propionitrile

Base Information

• Chemical Name: 3-[(1S)-1-(4-bromo-phenyl)-but-3-enyloxy]-propionitrile
• CAS No.: 913626-19-4
• Molecular Formula: C₁₃H₁₄BrNO
• Molecular Weight: 280.164
• Mol file: 913626-19-4.mol

Synonyms:3-[(1S)-1-(4-bromo-phenyl)-but-3-enyloxy]-propionitrile

Chemical Property of 3-[(1S)-1-(4-bromo-phenyl)-but-3-enyloxy]-propionitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-[(1S)-1-(4-bromo-phenyl)-but-3-enyloxy]-propionitrile

There total 1 articles about 3-[(1S)-1-(4-bromo-phenyl)-but-3-enyloxy]-propionitrile 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:

acrylonitrile (107-13-1,25014-41-9) + (S)-1-(4-bromophenyl)but-3-en-1-ol (221898-37-9) → 3-[(1S)-1-(4-bromo-phenyl)-but-3-enyloxy]-propionitrile (913626-19-4)

Guidance literature:

With N-benzyl-trimethylammonium hydroxide; In dichloromethane; water; at 20 - 25 ℃; for 2h;

DOI:10.1021/ol0618149

Reference yield: 96.0%

3-[(1S)-1-(4-bromo-phenyl)-but-3-enyloxy]-propionitrile (913626-19-4) + bromoacetic acid tert-butyl ester (5292-43-3) → 5-[1-(4-bromo-phenyl)-but-3-enyloxy]-3-oxo-pentanoic acid tert-butyl ester (913626-20-7)

Guidance literature:

With zinc; bis(cyclopentadienyl)titanium dichloride; In tetrahydrofuran; at 60 ℃; for 4h;

DOI:10.1021/ol0618149

Reference yield:

3-[(1S)-1-(4-bromo-phenyl)-but-3-enyloxy]-propionitrile (913626-19-4) → Octanoic acid (E)-(1S,5S,9S,11S,15R,19R,21S,24S)-1,15-dihydroxy-19-hydroxymethyl-23-[1-methoxycarbonyl-meth-(E)-ylidene]-2,2-dimethyl-17-oxo-11-phenyl-6,12,18,25,26-pentaoxa-tricyclo[19.3.1.15,9]hexacos-3-en-24-yl ester

Guidance literature:

Multi-step reaction with 9 steps

1.1: 96 percent / zinc / Cp₂TiCl₂ / tetrahydrofuran / 4 h / 60 °C

2.1: ozone / CH₂Cl₂ / 0.08 h / -78 °C

2.2: triphenylphosphine / CH₂Cl₂ / -78 - 20 °C

3.1: 1.8219 g / SnCl₄ / CH₂Cl₂ / 3.33 h / -78 - 25 °C

4.1: NaBH₄ / methanol / 0.33 h / 0 °C

5.1: 70 percent / lithium triethylborohydride / tetrahydrofuran / 1.75 h / 0 - 25 °C

6.1: 81 percent / 2,6-lutidine / CH₂Cl₂ / 23.67 h / -30 - 25 °C

7.1: 2,4,6-trichlorobenzoyl chloride; Et₃N / toluene / 4 h / 20 - 25 °C

7.2: 81 percent / DMAP / toluene / 1.75 h / 20 - 25 °C

8.1: 83 percent / HF*pyridine / tetrahydrofuran / 5.5 h / 0 - 25 °C

9.1: 24 percent / CsF / Pd(OAc)2; 2-dicyclohexylphosphino-2'-(N,N-dimethylamino)-biphenyl / dioxane / 53.8 h / 20 - 25 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; 2,4,6-trichlorobenzoyl chloride; tin(IV) chloride; lithium triethylborohydride; pyridine hydrogenfluoride; ozone; triethylamine; cesium fluoride; zinc; bis(cyclopentadienyl)titanium dichloride; palladium diacetate; DavePhos; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; toluene; 1.1: Blaise reaction / 3.1: Roskamp homologation / 9.1: Suzuki coupling;

DOI:10.1021/ol0618149

upstream raw materials:

acrylonitrile

(S)-1-(4-bromophenyl)but-3-en-1-ol

Downstream raw materials:

5-[1-(4-bromo-phenyl)-but-3-enyloxy]-3-oxo-pentanoic acid tert-butyl ester

(R)-5-[(1S,3S)-1-(4-Bromo-phenyl)-3,5-dihydroxy-pentyloxy]-3-hydroxy-pentanoic acid tert-butyl ester

5-(4-bromo-phenyl)-5-(4-tert-butoxycarbonyl-3-oxo-butoxy)-3-oxo-pentanoic acid ethyl ester

(3R,5S)-5-(4-Bromo-phenyl)-5-((R)-4-tert-butoxycarbonyl-3-hydroxy-butoxy)-3-hydroxy-pentanoic acid ethyl ester