1-(2-BROMOBENZYL)PYRROLIDINE

Base Information

• Chemical Name: 1-(2-BROMOBENZYL)PYRROLIDINE
• CAS No.: 91130-46-0
• Molecular Formula: C11H14BrN
• Molecular Weight: 240.143
• Hs Code.: 2933990090
• Mol file: 91130-46-0.mol

Synonyms:

Chemical Property of 1-(2-BROMOBENZYL)PYRROLIDINE

Chemical Property:

• PSA: 3.24000
• LogP: 2.98280

Purity/Quality:

98%min ^*data from raw suppliers

1-(2-Bromobenzyl)pyrrolidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-(2-BROMOBENZYL)PYRROLIDINE

There total 7 articles about 1-(2-BROMOBENZYL)PYRROLIDINE 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: 90.0%

o-bromobenzyl alcohol (18982-54-2) + rac-Pro-OH (609-36-9,25191-13-3,37159-97-0,4305-67-3,4607-28-7) → 1-bromo-2-(pyrrolidin-1-ylmethyl)benzene (91130-46-0)

Guidance literature:

With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; sodium hydrogencarbonate; In toluene; at 110 ℃; for 96h; Inert atmosphere;

DOI:10.1055/s-0033-1340474

Reference yield: 86.0%

pyrrolidine (123-75-1) + 1-Bromo-2-bromomethyl-benzene (3433-80-5) → 1-bromo-2-(pyrrolidin-1-ylmethyl)benzene (91130-46-0)

Guidance literature:

pyrrolidine; 1-Bromo-2-bromomethyl-benzene; In dichloromethane; for 24h;

With sodium hydroxide; In dichloromethane; for 0.5h;

DOI:10.1021/jacs.7b07519

Reference yield:

2-bromobenzoic acid chloride (7154-66-7) → 1-bromo-2-(pyrrolidin-1-ylmethyl)benzene (91130-46-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / Et₃N / CH₂Cl₂ / 2 h / Ambient temperature

2: 1.) borane-THF, 2.) aq. KOH / 1.) THF, reflux, 6 h, 2.) THF, MeOH, reflux, 1 h

With potassium hydroxide; borane-THF; triethylamine; In dichloromethane;

DOI:10.1016/S0957-4166(98)00394-2

upstream raw materials:

pyrrolidine

1-Bromo-2-bromomethyl-benzene

(2-bromophenyl)(pyrrolidin-1-yl)methanone

2-bromobenzoic acid chloride

Downstream raw materials:

phenanthridine

C₂₃H₃₂N₂

C₆H₄(CH₂BNC₄H₈)(NC₆H₃(CH(CH₃)2)2)

C₆H₄(CH₂N(CH₂)4)(NC₆H₃(CH(CH₃)2)2)BF₂

Refernces

• 1、 Evoniuk, Christopher J.,Hill, Sean P.,Hanson, Kenneth,Alabugin, Igor V.. "Double C-H amination by consecutive SET oxidations". . p. 7138 - 7141. Retrieved 2016/06/09.
• 2、 Yoshikai, Naohiko,Mieczkowski, Adam,Matsumoto, Arimasa,Ilies, Laurean,Nakamura, Eiichi. "Iron-catalyzed C-C bond formation at α-position of aliphatic amines via C-H bond activation through 1,5-hydrogen transfer". supporting information; experimental part. p. 5568 - 5569. Retrieved 2010/06/19.