(2E,4E)-4-methoxybenzyl 5-bromo-4-methylpenta-2,4-dienoate

Base Information

• Chemical Name: (2E,4E)-4-methoxybenzyl 5-bromo-4-methylpenta-2,4-dienoate
• CAS No.: 1312938-57-0
• Molecular Formula: C₁₄H₁₅BrO₃
• Molecular Weight: 311.175
• Mol file: 1312938-57-0.mol

Synonyms:(2E,4E)-4-methoxybenzyl 5-bromo-4-methylpenta-2,4-dienoate

Chemical Property of (2E,4E)-4-methoxybenzyl 5-bromo-4-methylpenta-2,4-dienoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2E,4E)-4-methoxybenzyl 5-bromo-4-methylpenta-2,4-dienoate

There total 2 articles about (2E,4E)-4-methoxybenzyl 5-bromo-4-methylpenta-2,4-dienoate 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: 92.0%

(2E,4E)-5-bromo-4-methylpenta-2,4-dienoic acid (1312938-56-9) + 4-Methoxybenzyl alcohol (105-13-5) → (2E,4E)-4-methoxybenzyl 5-bromo-4-methylpenta-2,4-dienoate (1312938-57-0)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 ℃; for 4h; Inert atmosphere;

DOI:10.1021/ol200964m

Reference yield:

(2E,4E)-methyl 5-bromo-4-methylpenta-2,4-dienoate (1312938-51-4) → (2E,4E)-4-methoxybenzyl 5-bromo-4-methylpenta-2,4-dienoate (1312938-57-0)

Guidance literature:

Multi-step reaction with 2 steps

1: water; sodium hydroxide / methanol / 3 h / 22 °C / Inert atmosphere

2: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 4 h / 0 °C / Inert atmosphere

With dmap; water; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium hydroxide; In methanol; dichloromethane;

DOI:10.1021/ol200964m

Reference yield: 82.0%

1-(4-dimethylaminophenyl)propan-1-one (26672-58-2) + (2E,4E)-4-methoxybenzyl 5-bromo-4-methylpenta-2,4-dienoate (1312938-57-0) + zinc(II) chloride (7646-85-7,24359-56-6) → (±)-(2E,4E)-methoxybenzyl 7-(4-(dimethylamino)phenyl)-4,6-dimethyl-7-oxohepta-2,4-dienoate (1312938-58-1)

Guidance literature:

1-(4-dimethylaminophenyl)propan-1-one; With 2,2,6,6-tetramethylpiperidinyl-lithium; In tetrahydrofuran; hexane; at 0 ℃; for 0.5h; Inert atmosphere;

zinc(II) chloride; In tetrahydrofuran; hexane; at 22 ℃; for 0.333333h; Inert atmosphere;

(2E,4E)-4-methoxybenzyl 5-bromo-4-methylpenta-2,4-dienoate; With 1,1'-bis(di-tertbutylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In tetrahydrofuran; hexane; at 22 ℃; for 1h; Inert atmosphere;

DOI:10.1021/ol200964m

upstream raw materials:

(2E,4E)-methyl 5-bromo-4-methylpenta-2,4-dienoate

(2E,4E)-5-bromo-4-methylpenta-2,4-dienoic acid

4-Methoxybenzyl alcohol

Downstream raw materials:

Trichostatic acid

(±)-(2E,4E)-methoxybenzyl 7-(4-(dimethylamino)phenyl)-4,6-dimethyl-7-oxohepta-2,4-dienoate