(Z)-1-bromo-4-(3-methylbut-1-en-1-yl)benzene

Base Information

• Chemical Name: (Z)-1-bromo-4-(3-methylbut-1-en-1-yl)benzene
• CAS No.: 1591938-63-4
• Molecular Formula: C₁₁H₁₃Br
• Molecular Weight: 225.128
• Mol file: 1591938-63-4.mol

Synonyms:(Z)-1-bromo-4-(3-methylbut-1-en-1-yl)benzene

Chemical Property of (Z)-1-bromo-4-(3-methylbut-1-en-1-yl)benzene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-1-bromo-4-(3-methylbut-1-en-1-yl)benzene

There total 3 articles about (Z)-1-bromo-4-(3-methylbut-1-en-1-yl)benzene 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:

1-((E)-2-Benzenesulfonyl-vinyl)-4-bromo-benzene (56361-12-7) + 4-isopropyl-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester (1539-32-8) → (E)-1-bromo-4-(3-methylbut-1-en-1-yl)benzene (1591938-65-6) + (Z)-1-bromo-4-(3-methylbut-1-en-1-yl)benzene (1591938-63-4)

Guidance literature:

With [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; In ethyl acetate; at 30 ℃; for 16h; Overall yield = 67 percent; Overall yield = 29.9 mg; Inert atmosphere; Irradiation;

DOI:10.1039/d1ob01806j

Reference yield:

isobutyltriphenylphosphonium bromide (22884-29-3) + 4-bromo-benzaldehyde (1122-91-4) → (E)-1-bromo-4-(3-methylbut-1-en-1-yl)benzene (1591938-65-6) + (Z)-1-bromo-4-(3-methylbut-1-en-1-yl)benzene (1591938-63-4)

Guidance literature:

isobutyltriphenylphosphonium bromide; With potassium tert-butylate; In tetrahydrofuran; toluene; for 4h; Inert atmosphere;

4-bromo-benzaldehyde; In tetrahydrofuran; toluene; at -78 - 20 ℃; for 3h; Overall yield = 88 %; Overall yield = 2.3 g; Inert atmosphere;

DOI:10.1021/ja5015508

Reference yield:

1-bromo-4-ethenyl-benzene (2039-82-9) → (E)-1-bromo-4-(3-methylbut-1-en-1-yl)benzene (1591938-65-6) + (Z)-1-bromo-4-(3-methylbut-1-en-1-yl)benzene (1591938-63-4)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium acetate; iodine / acetonitrile / Reflux; Inert atmosphere

2: [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate / ethyl acetate / 16 h / 30 °C / Inert atmosphere; Irradiation

With [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; iodine; sodium acetate; In ethyl acetate; acetonitrile;

DOI:10.1039/d1ob01806j

upstream raw materials:

isobutyltriphenylphosphonium bromide

4-bromo-benzaldehyde

1-((E)-2-Benzenesulfonyl-vinyl)-4-bromo-benzene

4-isopropyl-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester

Downstream raw materials:

1-bromo-4-isopentylbenzene

(2Z)-3-(4-bromophenyl)prop-2-enenitrile

Refernces

• 1、 Bess, Elizabeth N.,Deluca, Ryan J.,Tindall, Daniel J.,Oderinde, Martins S.,Roizen, Jennifer L.,Du Bois,Sigman, Matthew S.. "Analyzing site selectivity in Rh2(esp)2-catalyzed intermolecular C-H amination reactions". supporting information. p. 5783 - 5789. Retrieved 2014/05/06.