2,8-di-(m-bromophenyl)-5-acetylthiomethyl-1-aza-3,7-dioxabicyclo[3.3.0]octane

Base Information

• Chemical Name: 2,8-di-(m-bromophenyl)-5-acetylthiomethyl-1-aza-3,7-dioxabicyclo[3.3.0]octane
• CAS No.: 1311029-97-6
• Molecular Formula: C₂₀H₁₉Br₂NO₃S
• Molecular Weight: 513.25

Synonyms:2,8-di-(m-bromophenyl)-5-acetylthiomethyl-1-aza-3,7-dioxabicyclo[3.3.0]octane

Chemical Property of 2,8-di-(m-bromophenyl)-5-acetylthiomethyl-1-aza-3,7-dioxabicyclo[3.3.0]octane

Chemical Property:

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Technology Process of 2,8-di-(m-bromophenyl)-5-acetylthiomethyl-1-aza-3,7-dioxabicyclo[3.3.0]octane

There total 2 articles about 2,8-di-(m-bromophenyl)-5-acetylthiomethyl-1-aza-3,7-dioxabicyclo[3.3.0]octane 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%

2,8-di-(m-bromophenyl)-5-hydroxymethyl-1-aza-3,7-dioxabicyclo[3.3.0]octane (1311029-72-7) + tiolacetic acid (507-09-5) → 2,8-di-(m-bromophenyl)-5-acetylthiomethyl-1-aza-3,7-dioxabicyclo[3.3.0]octane (1311029-97-6)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In benzene; at 0 ℃; Reflux;

DOI:10.1021/jo2008498

Reference yield:

4-bromo-benzaldehyde (1122-91-4) → 2,8-di-(m-bromophenyl)-5-acetylthiomethyl-1-aza-3,7-dioxabicyclo[3.3.0]octane (1311029-97-6)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene-4-sulfonic acid / toluene / 12 h / Reflux

2: triphenylphosphine; diethylazodicarboxylate / benzene / 0 °C / Reflux

With toluene-4-sulfonic acid; triphenylphosphine; diethylazodicarboxylate; In toluene; benzene; 2: Mitsunobu reaction;

DOI:10.1021/jo2008498

Reference yield: 44.0%

2,8-di-(m-bromophenyl)-5-acetylthiomethyl-1-aza-3,7-dioxabicyclo[3.3.0]octane (1311029-97-6) → 2,8-di-(3-bromophenyl)-5-thiomethyl-1-aza-3,7-dioxabicyclo[3.3.0]octane (1311029-84-1) + bis-(2,8-di-(3-bromophenyl)-1-aza-3,7-dioxabicyclo[3.3.0]octane)-5-methyldisulfide (1311029-99-8)

Guidance literature:

With ammonia; In methanol; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1021/jo2008498

upstream raw materials:

2,8-di-(m-bromophenyl)-5-hydroxymethyl-1-aza-3,7-dioxabicyclo[3.3.0]octane

tiolacetic acid

4-bromo-benzaldehyde

Downstream raw materials:

2,8-bis(3-bromophenyl)-7,9-dioxa-3-thia-1-azaspiro-[4.5]decane

2,8-di-(3-bromophenyl)-5-thiomethyl-1-aza-3,7-dioxabicyclo[3.3.0]octane

bis-(2,8-di-(3-bromophenyl)-1-aza-3,7-dioxabicyclo[3.3.0]octane)-5-methyldisulfide

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