(4Z)-4-(3-bromo-4-hydroxy-5-methoxybenzylidene)-1-(4-methylphenyl)pyrazolidine-3,5-dione

Base Information

• Chemical Name: (4Z)-4-(3-bromo-4-hydroxy-5-methoxybenzylidene)-1-(4-methylphenyl)pyrazolidine-3,5-dione
• CAS No.: 5628-12-6
• Molecular Formula: C18H15BrN2O4
• Molecular Weight: 238.329
• Mol file: 5628-12-6.mol

Synonyms:methoxy[2,2]paracyclophane;4-Methoxy-<2,2>paracyclophan;4-Methoxy-<2.2>-paracyclophan;4-Methoxy-[2.2]-paracyclophan;5-Methoxy-tricyclo[8.2.2.24,7]hexadeca-1(13),4(16),5,7(15),10(14),11-hexaene;

Chemical Property of (4Z)-4-(3-bromo-4-hydroxy-5-methoxybenzylidene)-1-(4-methylphenyl)pyrazolidine-3,5-dione

Chemical Property:

• Melting Point: 114 °C
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 9.23000
• Density: 1.577g/cm³
• LogP: 3.57900

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (4Z)-4-(3-bromo-4-hydroxy-5-methoxybenzylidene)-1-(4-methylphenyl)pyrazolidine-3,5-dione

There total 1 articles about (4Z)-4-(3-bromo-4-hydroxy-5-methoxybenzylidene)-1-(4-methylphenyl)pyrazolidine-3,5-dione 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:

(7-methoxy[2.2]paracyclophan-4-yl)(4'-methoxyphenyl)iodonium hexafluorophosphate + sodium phenoxide (139-02-6) → para-iodoanisole (696-62-8) + 1-methoxy-4-phenoxy-benzene (1655-69-2) + 4-methoxy-7-iodo[2.2]paracyclophane (1235887-94-1) + 4-methoxy[2.2]paracyclophane (5628-12-6)

Guidance literature:

In [D₃]acetonitrile; at 45 ℃; regioselective reaction; Inert atmosphere; Darkness;

DOI:10.1002/anie.201000695

Reference yield:

4-methoxy[2.2]paracyclophane (5628-12-6) → (7-methoxy[2.2]paracyclophan-4-yl)(4'-methoxyphenyl)iodonium hexafluorophosphate

Guidance literature:

Multi-step reaction with 2 steps

1.1: N-Bromosuccinimide; trifluoroacetic acid / dichloromethane / 0.5 h / 20 °C / Darkness

2.1: tert.-butyl lithium / diethyl ether / 1 h / -78 °C / Inert atmosphere

2.2: -78 - 20 °C / Inert atmosphere

With N-Bromosuccinimide; tert.-butyl lithium; trifluoroacetic acid; In diethyl ether; dichloromethane;

DOI:10.1021/ol201080c

Reference yield:

4-methoxy[2.2]paracyclophane (5628-12-6) → C24H24FIO2

Guidance literature:

Multi-step reaction with 3 steps

1.1: N-Bromosuccinimide; trifluoroacetic acid / dichloromethane / 0.5 h / 20 °C / Darkness

2.1: tert.-butyl lithium / diethyl ether / 1 h / -78 °C / Inert atmosphere

2.2: -78 - 20 °C / Inert atmosphere

3.1: tetramethylammonium fluoride / acetonitrile / Inert atmosphere; Glove box

With N-Bromosuccinimide; tetramethylammonium fluoride; tert.-butyl lithium; trifluoroacetic acid; In diethyl ether; dichloromethane; acetonitrile;

DOI:10.1021/ol201080c

upstream raw materials:

sodium phenoxide

Downstream raw materials:

(rac)-N-{7-methoxy([2.2]paracyclophane-4-yl)methylene}aniline