3-(2-bromo-4,5-dihydroxyphenyl)propionitrile

Base Information

• Chemical Name: 3-(2-bromo-4,5-dihydroxyphenyl)propionitrile
• CAS No.: 84003-65-6
• Molecular Formula: C₉H₈BrNO₂
• Molecular Weight: 242.072
• Mol file: 84003-65-6.mol

Synonyms:3-(2-bromo-4,5-dihydroxyphenyl)propionitrile

Chemical Property of 3-(2-bromo-4,5-dihydroxyphenyl)propionitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(2-bromo-4,5-dihydroxyphenyl)propionitrile

There total 1 articles about 3-(2-bromo-4,5-dihydroxyphenyl)propionitrile 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: 84.0%

3-(2-bromo-4,5-dimethoxyphenyl)propanenitrile (35249-62-8) → 3-(2-bromo-4,5-dihydroxyphenyl)propionitrile (84003-65-6)

Guidance literature:

With boron tribromide; In dichloromethane; for 3h; Ambient temperature;

DOI:10.1002/recl.19821010903

Reference yield: 96.0%

benzyl bromide (100-39-0) + 3-(2-bromo-4,5-dihydroxyphenyl)propionitrile (84003-65-6) → 3-<2-bromo-4,5-bis(benzyloxy)phenyl>propionitrile (81615-12-5)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; for 16h;

DOI:10.1002/recl.19821010903

Reference yield:

3-(2-bromo-4,5-dihydroxyphenyl)propionitrile (84003-65-6) → cis-7,8-bis(benzyloxy)-2-propyl-1,2,3,3a,5,9b-hexahydro<2>benzopyrano<3,4-c>pyrrole

Guidance literature:

Multi-step reaction with 9 steps

1: 96 percent / potassium carbonate / dimethylformamide / 16 h

2: 61 percent / sodium amide / Fe(NO₃)3 / liquid ammonia / 1.5 h / -33 °C

3: 93 percent / aq. KOH; ethanol / 16 h / Heating

4: thionyl chloride / dimethyl formamide / 1.) room temp., 1 h; 2.) reflux, 15 min

5: 79 percent / triethylamine / CH₂Cl₂ / 1.) -50 deg C, 0.5 h; 2.) room temp., 1 h

6: 94 percent / dimethyl sulfoxide, oxalyl chloride, triethylamine / CH₂Cl₂ / 0.5 h / Ambient temperature

7: 8.4 g / various solvent(s) / 16 h / Heating

8: DBN / toluene / 0.17 h / 80 °C

9: 1.4 g / borane-dimethyl sulfide / tetrahydrofuran / 6 h / Heating

With thionyl chloride; oxalyl dichloride; 2,6-dichloro-benzonitrile; dimethylsulfide borane complex; potassium carbonate; sodium amide; dimethyl sulfoxide; triethylamine; ferric nitrate; N,N-dimethyl-formamide; In tetrahydrofuran; potassium hydroxide; ethanol; dichloromethane; ammonia; N,N-dimethyl-formamide; toluene;

DOI:10.1002/recl.19821010903

upstream raw materials:

3-(2-bromo-4,5-dimethoxyphenyl)propanenitrile

Downstream raw materials:

3-<2-bromo-4,5-bis(benzyloxy)phenyl>propionitrile

3,4-bis(benzyloxy)-7-(hydroxymethyl)bicyclo<4.2.0>octa-1,3,5-triene

3,4-bis(benzyloxy)bicyclo<4.2.0>octa-1,3,5-triene-7-carbonitrile

3,4-bis(benzyloxy)bicyclo<4.2.0>octa-1,3,5-triene-7-carboxylic acid

Refernces