4-Bromo-benzoic acid (2R,4S,6S,12R)-4-acetoxymethyl-15-isopropenyl-12-methyl-9-methylene-5-oxa-tricyclo[10.3.0.0^4,6]pentadec-1⁽¹⁵⁾-en-2-yl ester

Base Information

• Chemical Name: 4-Bromo-benzoic acid (2R,4S,6S,12R)-4-acetoxymethyl-15-isopropenyl-12-methyl-9-methylene-5-oxa-tricyclo[10.3.0.0^4,6]pentadec-1⁽¹⁵⁾-en-2-yl ester
• CAS No.: 112661-64-0
• Molecular Formula: C₂₉H₃₅BrO₅
• Molecular Weight: 543.498

Synonyms:

Chemical Property of 4-Bromo-benzoic acid (2R,4S,6S,12R)-4-acetoxymethyl-15-isopropenyl-12-methyl-9-methylene-5-oxa-tricyclo[10.3.0.0^4,6]pentadec-1⁽¹⁵⁾-en-2-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-Bromo-benzoic acid (2R,4S,6S,12R)-4-acetoxymethyl-15-isopropenyl-12-methyl-9-methylene-5-oxa-tricyclo[10.3.0.0^4,6]pentadec-1⁽¹⁵⁾-en-2-yl ester

There total 4 articles about 4-Bromo-benzoic acid (2R,4S,6S,12R)-4-acetoxymethyl-15-isopropenyl-12-methyl-9-methylene-5-oxa-tricyclo[10.3.0.0^4,6]pentadec-1⁽¹⁵⁾-en-2-yl ester 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:

Acetic acid (2R,4S,6S,12R)-2-hydroxy-15-isopropenyl-12-methyl-9-methylene-5-oxa-tricyclo[10.3.0.04,6]pentadec-1(15)-en-4-ylmethyl ester (112661-63-9) + 4-chlorobenzoyl chloride (586-75-4) → 4-Bromo-benzoic acid (2R,4S,6S,12R)-4-acetoxymethyl-15-isopropenyl-12-methyl-9-methylene-5-oxa-tricyclo[10.3.0.04,6]pentadec-1(15)-en-2-yl ester (112661-64-0)

Guidance literature:

With dmap; In pyridine; at 65 ℃; for 9h;

DOI:10.1248/cpb.36.2840

Reference yield:

stolonidiol (112661-59-3) → 4-Bromo-benzoic acid (2R,4S,6S,12R)-4-acetoxymethyl-15-isopropenyl-12-methyl-9-methylene-5-oxa-tricyclo[10.3.0.04,6]pentadec-1(15)-en-2-yl ester (112661-64-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 17 mg / pyridine / 20 h / Ambient temperature

2: 11 mg / phosphorous oxychloride / pyridine / 3 h / 30 °C

3: 2.2 mg / N,N-dimethylaminopyridine / pyridine / 9 h / 65 °C

With dmap; trichlorophosphate; In pyridine;

DOI:10.1248/cpb.36.2840

Reference yield:

stolonidiol monoacetate (112692-67-8) → 4-Bromo-benzoic acid (2R,4S,6S,12R)-4-acetoxymethyl-15-isopropenyl-12-methyl-9-methylene-5-oxa-tricyclo[10.3.0.04,6]pentadec-1(15)-en-2-yl ester (112661-64-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 11 mg / phosphorous oxychloride / pyridine / 3 h / 30 °C

2: 2.2 mg / N,N-dimethylaminopyridine / pyridine / 9 h / 65 °C

With dmap; trichlorophosphate; In pyridine;

DOI:10.1248/cpb.36.2840

upstream raw materials:

Acetic acid (2R,4S,6S,12R)-2-hydroxy-15-isopropenyl-12-methyl-9-methylene-5-oxa-tricyclo[10.3.0.0^4,6]pentadec-1⁽¹⁵⁾-en-4-ylmethyl ester

4-chlorobenzoyl chloride

stolonidiol

stolonidiol monoacetate

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