2-Bromo-N-[(diphenylphosphinyl)methyl]-N-[(4-methoxyphenyl)methyl]-5-(phenylmethoxy)benzamide

Base Information

• Chemical Name: 2-Bromo-N-[(diphenylphosphinyl)methyl]-N-[(4-methoxyphenyl)methyl]-5-(phenylmethoxy)benzamide
• CAS No.: 286434-57-9
• Molecular Formula: C35H31BrNO4P
• Molecular Weight: 640.513
• DSSTox Substance ID: DTXSID701118833
• Nikkaji Number: J1.410.827K
• Mol file: 286434-57-9.mol

Synonyms:DTXSID701118833;286434-57-9;2-Bromo-N-[(diphenylphosphinyl)methyl]-N-[(4-methoxyphenyl)methyl]-5-(phenylmethoxy)benzamide

Chemical Property of 2-Bromo-N-[(diphenylphosphinyl)methyl]-N-[(4-methoxyphenyl)methyl]-5-(phenylmethoxy)benzamide

Chemical Property:

• XLogP3: 7.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 11
• Exact Mass: 639.11741
• Heavy Atom Count: 42
• Complexity: 839

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)CN(CP(=O)(C2=CC=CC=C2)C3=CC=CC=C3)C(=O)C4=C(C=CC(=C4)OCC5=CC=CC=C5)Br

Technology Process of 2-Bromo-N-[(diphenylphosphinyl)methyl]-N-[(4-methoxyphenyl)methyl]-5-(phenylmethoxy)benzamide

There total 2 articles about 2-Bromo-N-[(diphenylphosphinyl)methyl]-N-[(4-methoxyphenyl)methyl]-5-(phenylmethoxy)benzamide 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:

5-(benzyloxy)-2-bromobenzoic acid → 5-benzyloxy-2-bromo-N-(diphenyl-phosphinoylmethyl)-N-(4-methoxy-benzyl)-benzamide (286434-57-9)

Guidance literature:

Multi-step reaction with 2 steps

1: SOCl₂; DMF / CH₂Cl₂

With thionyl chloride; N,N-dimethyl-formamide; In dichloromethane; 1: Substitution / 2: Acylation;

DOI:10.1055/s-2000-6385

Reference yield:

N-[(diphenylphosphinoyl)methyl]-N-(4-methoxybenzyl)amine (195005-12-0) + 5-benzyloxy-2-bromo-benzoyl chloride (886447-22-9) → 5-benzyloxy-2-bromo-N-(diphenyl-phosphinoylmethyl)-N-(4-methoxy-benzyl)-benzamide (286434-57-9)

Guidance literature:

DOI:10.1055/s-2000-6385

Reference yield: 73.0%

5-benzyloxy-2-bromo-N-(diphenyl-phosphinoylmethyl)-N-(4-methoxy-benzyl)-benzamide (286434-57-9) → 6-benzyloxy-2-(4-methoxy-benzyl)-2,3-dihydro-isoindol-1-one

Guidance literature:

5-benzyloxy-2-bromo-N-(diphenyl-phosphinoylmethyl)-N-(4-methoxy-benzyl)-benzamide; With potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -78 - 20 ℃; for 2.5h;

With sodium hydroxide; water; In tetrahydrofuran; toluene; for 3h; Heating;

DOI:10.1055/s-2000-6385

upstream raw materials:

N-[(diphenylphosphinoyl)methyl]-N-(4-methoxybenzyl)amine

5-benzyloxy-2-bromo-benzoyl chloride

Downstream raw materials:

6-Benzyloxy-3-[1-(4-benzyloxy-2-bromo-3,5-dimethoxy-phenyl)-meth-(E)-ylidene]-2-(4-methoxy-benzyl)-2,3-dihydro-isoindol-1-one