(R)-2-(4-bromo-phenyl)-2-cyclopropylpropionitrile

Base Information

• Chemical Name: (R)-2-(4-bromo-phenyl)-2-cyclopropylpropionitrile
• CAS No.: 1360551-90-1
• Molecular Formula: C₁₂H₁₂BrN
• Molecular Weight: 250.138
• Mol file: 1360551-90-1.mol

Synonyms:(R)-2-(4-bromo-phenyl)-2-cyclopropylpropionitrile

Chemical Property of (R)-2-(4-bromo-phenyl)-2-cyclopropylpropionitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-(4-bromo-phenyl)-2-cyclopropylpropionitrile

There total 12 articles about (R)-2-(4-bromo-phenyl)-2-cyclopropylpropionitrile 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:

2-(4-bromo-phenyl)-2-cyclopropylpropionitrile (1360551-88-7) → (S)-2-(4-bromo-phenyl)-2-cyclopropylpropionitrile (1360551-91-2) + (R)-2-(4-bromo-phenyl)-2-cyclopropylpropionitrile (1360551-90-1)

Guidance literature:

With ChiralPak AY-H 300x20mm SFC column; In ethanol; Purification / work up; Resolution of racemate;

Reference yield:

1-(4-bromophenyl)-1-cyclopropylethan-1-ol (56041-75-9) → (R)-2-(4-bromo-phenyl)-2-cyclopropylpropionitrile (1360551-90-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: boron trifluoride diethyl etherate / dichloromethane / 3.83 h / -75 - 20 °C / Large scale

2.1: potassium hydroxide / water; propan-1-ol / 145 °C / 6750.68 Torr / Autoclave; Large scale

2.2: 4 h / 20 - 60 °C / Large scale

3.1: hydrogenchloride / water; tert-butyl methyl ether / 1 h / Large scale

3.2: 25 - 80 °C / Resolution of racemate; Large scale

4.1: hydrogenchloride / water; toluene / 1 h / 20 °C / Large scale

4.2: 1 h / 47 °C / Large scale

5.1: ammonia / toluene / 2 h / -10 - 20 °C / Large scale

6.1: trifluoroacetic anhydride; pyridine / toluene / 1 h / 10 - 20 °C / Large scale

With pyridine; hydrogenchloride; boron trifluoride diethyl etherate; ammonia; trifluoroacetic anhydride; potassium hydroxide; In propan-1-ol; dichloromethane; tert-butyl methyl ether; water; toluene;

DOI:10.1021/acs.oprd.7b00202

Reference yield:

C11H10BrN → (R)-2-(4-bromo-phenyl)-2-cyclopropylpropionitrile (1360551-90-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 °C / Inert atmosphere

1.2: methyl halide / 16 h / Inert atmosphere; Heating

2.1: carbon dioxide / ethanol / 38 °C / 75007.5 Torr / Resolution of racemate

With carbon dioxide; sodium hydride; In ethanol; N,N-dimethyl-formamide; mineral oil;

DOI:10.1021/jm501185j

upstream raw materials:

(4-bromophenyl)(cyclopropyl)methanone

1-(4-bromophenyl)-1-cyclopropylethan-1-ol

2-(4-bromo-phenyl)-2-cyclopropylpropionitrile

1.4-dibromobenzene

Downstream raw materials:

(R)-2-[4-(2-aminopyrimidin-5-yl)phenyl]-2-cyclopropylpropionitrile

C₁₇H₁₈N₄

2-{2-[4-(3-{(R)-1-[4-(2-amino-pyrimidin-5-yl)-phenyl]-1-cyclopropyl-ethyl}-[1,2,4]oxadiazol-5-yl)-pyrazol-1-yl]-ethyl}-isoindole-1,3-dione

5-(4-{(R)-1-cyclopropyl-1-[5-(1H-pyrazol-4-yl)-[1,2,4]oxadiazol-3-yl]ethyl}phenyl)pyrimidin-2-ylamine