Benzaldehyde, 2-bromo-4-methoxy-3-(phenylmethoxy)-

Base Information

• Chemical Name: Benzaldehyde, 2-bromo-4-methoxy-3-(phenylmethoxy)-
• CAS No.: 38849-38-6
• Molecular Formula: C15H13BrO3
• Molecular Weight: 321.17
• Mol file: 38849-38-6.mol

Synonyms:

Chemical Property of Benzaldehyde, 2-bromo-4-methoxy-3-(phenylmethoxy)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzaldehyde, 2-bromo-4-methoxy-3-(phenylmethoxy)-

There total 4 articles about Benzaldehyde, 2-bromo-4-methoxy-3-(phenylmethoxy)- 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: 100.0%

2-bromoisovanillin (2973-58-2) + benzyl chloride (100-44-7) → 3-(benzyloxy)-2-bromo-4-methoxybenzaldehyde (38849-38-6)

Guidance literature:

With potassium carbonate; In ethanol; for 4h; Reflux; Inert atmosphere;

DOI:10.1055/s-0029-1217393

Reference yield: 100.0%

2-bromoisovanillin (2973-58-2) + benzyl bromide (100-39-0) → 3-(benzyloxy)-2-bromo-4-methoxybenzaldehyde (38849-38-6)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; Inert atmosphere;

Reference yield:

isovanillin (621-59-0) → 3-(benzyloxy)-2-bromo-4-methoxybenzaldehyde (38849-38-6)

Guidance literature:

Multi-step reaction with 2 steps

1: bromine / acetic acid / 0 - 20 °C

2: potassium carbonate / acetone / 3 h / Reflux

With bromine; potassium carbonate; In acetic acid; acetone;

DOI:10.1021/ol102521q

upstream raw materials:

2-bromoisovanillin

benzyl bromide

benzyl chloride

isovanillin

Downstream raw materials:

2,2′-diformyl-5,5′-dimethoxy-6,6′-bis(phenylmethoxy)biphenyl

Carbonic acid 2'-benzyloxy-6,6'-diformyl-3,3'-dimethoxy-5-methyl-biphenyl-2-yl ester methyl ester

3-(benzyloxy)-2-bromo-4-methoxybenzoic acid

3-benzyloxy-4-methoxybenzaldehyde

Refernces

Synthesis of models related to taspine

10.1080/00397919108019768

The research details the synthesis of diphenylic compounds related to the alkaloid taspine, an alkaloid with an unusual diphenylic skeleton that had not been previously synthesized. The study aimed to address the challenges in taspine synthesis, such as asymmetric diphenylic coupling and steric hindrance, by synthesizing simplified models. The researchers reported the synthesis of compound 2, which carries a methyl group instead of the 2-(N-dimethylamino)-ethyl group present in taspine, and the symmetric lactone 32, obtained as a by-product. Key chemicals used in the process included 2-bromo-4-methoxy-3-methoxycarbonyloxy-6-methylbenzaldehyde (S3), 3-benzyloxy-2-bromo-4-methoxybenzaldehyde (6), and various other derivatives and reagents such as copper bronze for the Ullmann reaction, Jones' reagent for oxidation, and hydrogenolysis for the removal of benzyl groups. The final products, dilactones 2 and 3, were obtained in high yields and were found to be insoluble in most solvents, with properties differing from those previously reported for similar structures.