2-(3-Methoxypropoxy)-4-((R)-2-(bromomethyl)-3-methylbutyl)-1-methoxybenzene

Base Information

• Chemical Name: 2-(3-Methoxypropoxy)-4-((R)-2-(bromomethyl)-3-methylbutyl)-1-methoxybenzene
• CAS No.: 172900-69-5
• Molecular Formula: C17H27BrO3
• Molecular Weight: 359.304
• Hs Code.: 2909309090
• DSSTox Substance ID: DTXSID90462476
• Nikkaji Number: J1.947.302C
• Wikidata: Q72518134
• Mol file: 172900-69-5.mol

Synonyms:172900-69-5;2-(3-Methoxypropoxy)-4-((R)-2-(bromomethyl)-3-methylbutyl)-1-methoxybenzene;4-[(2R)-2-(Bromomethyl)-3-methylbutyl]-1-methoxy-2-(3-methoxypropoxy)benzene;1-METHOXY-2-(3-METHOXYPROPOXY)-4-[(3-BROMO-(2R)-ISOPROPYL)PROPYL]BENZENE;C17H27BrO3;SCHEMBL4300111;DTXSID90462476;BCP22237;MFCD10566721;(R)-4-[2-(Bromomethyl)-3-methylbutyl]-1-methoxy-2-(3-methoxypropoxy)benzene;AKOS015851736;AKOS015888737;DS-12503;AM20090747;CS-0154346;C73317;J-010862;(R)-2-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-3-methyl-butyl bromide;2(R)-[4-methoxy-3-(3-methoxypropoxy)-benzyl]-3-methyl-butyl bromide;1-Methoxy-2-(3-methoxypropoxy)-4-[(R)-2-(bromomethyl)-3-methylbutyl]benzene;4-((R)-2-bromomethyl-3-methyl-butyl)-1-methoxy-2-(3-methoxy-propoxy)-benzene;4-[(2R)-2-(bromomethyl)-3-methyl-butyl]-1-methoxy-2-(3-methoxypropoxy)benzene;Benzene, 4-[(2R)-2-(bromomethyl)-3-methylbutyl]-1-methoxy-2-(3-methoxypropoxy)-

Chemical Property of 2-(3-Methoxypropoxy)-4-((R)-2-(bromomethyl)-3-methylbutyl)-1-methoxybenzene

Chemical Property:

• Vapor Pressure: 3.29E-06mmHg at 25°C
• Melting Point: 52-53 °C
• Refractive Index: 1.506
• Boiling Point: 398.8 °C at 760 mmHg
• Flash Point: 164.4 °C
• PSA: 27.69000
• Density: 1.173 g/cm³
• LogP: 4.32010
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: Dichloromethane, Ethyl Acetate,
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 10
• Exact Mass: 358.11436
• Heavy Atom Count: 21
• Complexity: 260

Purity/Quality:

99% ^*data from raw suppliers

1-Methoxy-2-(3-methoxypropoxy)-4-[(3-bromo-(2R)-isopropyl)propyl]benzene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(CC1=CC(=C(C=C1)OC)OCCCOC)CBr
• Isomeric SMILES: CC(C)[C@@H](CC1=CC(=C(C=C1)OC)OCCCOC)CBr
• Uses: Intermediate in the preparation of Aliskiren.

Technology Process of 2-(3-Methoxypropoxy)-4-((R)-2-(bromomethyl)-3-methylbutyl)-1-methoxybenzene

There total 17 articles about 2-(3-Methoxypropoxy)-4-((R)-2-(bromomethyl)-3-methylbutyl)-1-methoxybenzene 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: 97.0%

(R)-2-[4-methoxy-3-(3-methoxypropoxy)benzyl]-3-methylbutanol (172900-70-8) → (R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene (172900-69-5)

Guidance literature:

With N-Bromosuccinimide; triphenylphosphine; In dichloromethane; at 20 ℃; for 18h;

DOI:10.1002/hlca.200390235

Reference yield:

4-methoxy-3-(3-methoxypropoxy)benzaldehyde (172900-75-3) → (R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene (172900-69-5)

Guidance literature:

Multi-step reaction with 6 steps

1: NaBH₄ / ethanol

2: PBr₃ / CH₂Cl₂

3: 76 percent / LiHMDS / tetrahydrofuran

4: 81 percent / LiOH; H₂O₂

5: 95 percent / LAH / tetrahydrofuran

6: 97 percent / PPh₃; NBS / CH₂Cl₂

With lithium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; lithium aluminium tetrahydride; dihydrogen peroxide; phosphorus tribromide; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1016/j.tetlet.2005.07.028

Reference yield:

4-(bromomethyl)-1-methoxy-2-(3-methoxypropoxy)-benzene (172900-73-1) → (R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene (172900-69-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 76 percent / LiHMDS / tetrahydrofuran

2: 81 percent / LiOH; H₂O₂

3: 95 percent / LAH / tetrahydrofuran

4: 97 percent / PPh₃; NBS / CH₂Cl₂

With lithium hydroxide; N-Bromosuccinimide; lithium aluminium tetrahydride; dihydrogen peroxide; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tetlet.2005.07.028

upstream raw materials:

(R)-2-[4-methoxy-3-(3-methoxypropoxy)benzyl]-3-methylbutanol

isovanillin

(R)-4-benzyl-3-(3-methylbutyryl)oxazolidin-2-one

4-methoxy-3-(3-methoxypropoxy)benzaldehyde

Downstream raw materials:

(2S)-3,6-diethoxy-2,5-dihydro-2-{(2S)-2-{[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-3-methylbutyl}-pyrazine

(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester

(2S,4S)-2-tert-butoxycarbonylamino-4-[4-methoxy-3-(3-methoxypropoxy)benzyl]-5-methylhexanoic acid

[(1S,3S)-3-[4-Methoxy-3-(3-methoxy-propoxy)-benzyl]-1-(methoxy-methyl-carbamoyl)-4-methyl-pentyl]-carbamic acid tert-butyl ester

Refernces

• 1、 Wang, Fan,Xu, Xiao-Ying,Wang, Fei-Ying,Peng, Lin,Zhang, Yong,Tian, Fang,Wang, Li-Xin. "An improved and economical process for the manufacture of the key intermediate of aliskiren, a new potent renin inhibitor". . p. 1458 - 1462. Retrieved 2013/12/04.
• 2、 -. "PROCESS FOR THE PREPARATION OF (2S,4S,5S,7S)-N-(2-CARBAMYL-2- METHYLPROPYL)-5-AMINO-4-HYDROXY-2,7-DIISOPROPYL-8-[4-METHOXY-3-(3- METHOXYPROPOXY)PHENYL]-OCTANAMIDE HEMIFUMARATE AND ITS INTERMEDIATES THEREOF". Page/Page column 62. . Retrieved 2011/12/14.