2-Bromo-4-methoxy-5-(1-methylethoxy)benzene Acetonitrile

Base Information

• Chemical Name: 2-Bromo-4-methoxy-5-(1-methylethoxy)benzene Acetonitrile
• CAS No.: 365572-35-6
• Molecular Formula: C12H14BrNO2
• Molecular Weight: 284.153
• DSSTox Substance ID: DTXSID90473840
• Wikidata: Q82303488
• Mol file: 365572-35-6.mol

Synonyms:2-Bromo-4-methoxy-5-(1-methylethoxy)benzene Acetonitrile;365572-35-6;SCHEMBL5361609;DTXSID90473840;HMIMQSYMUHXERW-UHFFFAOYSA-N;AKOS000277737

Chemical Property of 2-Bromo-4-methoxy-5-(1-methylethoxy)benzene Acetonitrile

Chemical Property:

• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 283.02079
• Heavy Atom Count: 16
• Complexity: 261

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)OC1=C(C=C(C(=C1)CC#N)Br)OC

Technology Process of 2-Bromo-4-methoxy-5-(1-methylethoxy)benzene Acetonitrile

There total 1 articles about 2-Bromo-4-methoxy-5-(1-methylethoxy)benzene Acetonitrile 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: 95.0%

potassium cyanide (151-50-8) + 1-bromo-2-(chloromethyl)-5-methoxy-4-(1-methylethoxy)benzene (365572-07-2) → 2-bromo-4-methoxy-5-(1-methylethoxy)benzeneacetonitrile (365572-35-6)

Guidance literature:

In dimethyl sulfoxide; at 20 ℃; for 12h;

DOI:10.1002/jhet.5570390626

Reference yield: 71.0%

1-(3-iodopropyl)-4-(1-methylethoxy)benzene (365572-37-8) + 2-bromo-4-methoxy-5-(1-methylethoxy)benzeneacetonitrile (365572-35-6) → α-[2-bromo-4-methoxy-5-(1-methylethoxy)phenyl]4-(1-methylethoxy)benzenepentanenitrile (365572-38-9)

Guidance literature:

2-bromo-4-methoxy-5-(1-methylethoxy)benzeneacetonitrile; With n-butyllithium; diisopropylamine; In tetrahydrofuran; at -78 - 20 ℃;

1-(3-iodopropyl)-4-(1-methylethoxy)benzene; In tetrahydrofuran; at -78 ℃; for 1h;

DOI:10.1002/jhet.5570390626

Reference yield:

2-bromo-4-methoxy-5-(1-methylethoxy)benzeneacetonitrile (365572-35-6) → α-[2-bromo-5-hydroxy-4-methoxyphenyl]-4-hydroxybenzenepentanamide (365572-40-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: n-butyllithium; diisopropylamine / tetrahydrofuran / -78 - 20 °C

1.2: 71 percent / tetrahydrofuran / 1 h / -78 °C

2.1: aq. KOH / ethanol / 6 h / Heating

3.1: oxalyl chloride; DMF / CH₂Cl₂ / 2 h / 0 °C

3.2: 26.0 g / NH₃ / tetrahydrofuran / 2 h

4.1: 99 percent / BCl₃ / CH₂Cl₂ / -78 - 20 °C

With potassium hydroxide; n-butyllithium; oxalyl dichloride; boron trichloride; diisopropylamine; N,N-dimethyl-formamide; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1002/jhet.5570390626

upstream raw materials:

potassium cyanide

1-bromo-2-(chloromethyl)-5-methoxy-4-(1-methylethoxy)benzene

Downstream raw materials:

α-[2-bromo-4-methoxy-5-(1-methylethoxy)phenyl]4-(1-methylethoxy)benzenepentanenitrile

α-[2-bromo-5-hydroxy-4-methoxyphenyl]-4-hydroxybenzenepentanamide

α-[2-bromo-4-methoxy-5-(1-methylethoxy)phenyl]4-(1-methylethoxy)benzenepentanamide

Refernces