(3S,5R,8S)-3,8-bis(bromomethyl)-3,8-di-o-tolyl-2,7-dioxaspiro[4.4]nonan-1-one

Base Information

Chemical Name:(3S,5R,8S)-3,8-bis(bromomethyl)-3,8-di-o-tolyl-2,7-dioxaspiro[4.4]nonan-1-one
CAS No.:1643718-43-7
Molecular Formula:C₂₃H₂₄Br₂O₃
Molecular Weight:508.25
Hs Code.:

Synonyms:

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Chemical Property of (3S,5R,8S)-3,8-bis(bromomethyl)-3,8-di-o-tolyl-2,7-dioxaspiro[4.4]nonan-1-one

Chemical Property:

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Technology Process of (3S,5R,8S)-3,8-bis(bromomethyl)-3,8-di-o-tolyl-2,7-dioxaspiro[4.4]nonan-1-one

There total 5 articles about (3S,5R,8S)-3,8-bis(bromomethyl)-3,8-di-o-tolyl-2,7-dioxaspiro[4.4]nonan-1-one 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:

: 1643718-57-3
dimethyl 2,2-bis(2-(o-tolyl)allyl)malonate

: 1643718-43-7
(3S,5R,8S)-3,8-bis(bromomethyl)-3,8-di-o-tolyl-2,7-dioxaspiro[4.4]nonan-1-one

: 3,8-bis(bromomethyl)-3,8-di-o-tolyl-2,7-dioxaspiro[4.4]nonan-1-one

Guidance literature:: Multi-step reaction with 5 steps

1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 25 °C / Inert atmosphere

2: N-bromophthalimide; C₃₂H₃₉N₃O₃S / chloroform; hexane / 12 h / -60 °C / Inert atmosphere; Molecular sieve; Darkness

3: pyridinium chlorochromate / dichloromethane / Molecular sieve

4: sodium dihydrogenphosphate; sodium chlorite / tert-butyl alcohol; water / 2 h

5: N-Bromosuccinimide; triphenylphosphine sulfide / dichloromethane / 12 h / -50 °C / Darkness

With sodium chlorite; sodium dihydrogenphosphate; N-Bromosuccinimide; lithium aluminium tetrahydride; N-bromophthalimide; C₃₂H₃₉N₃O₃S; triphenylphosphine sulfide; pyridinium chlorochromate; In tetrahydrofuran; hexane; dichloromethane; chloroform; water; tert-butyl alcohol;
DOI:10.1002/anie.201310136

Reference yield:

: 1643718-31-3
((3R,5S)-5-(bromomethyl)-5-(o-tolyl)-3-(2-(o-tolyl)allyl)tetrahydrofuran-3-yl)methanol

: 1643718-43-7
(3S,5R,8S)-3,8-bis(bromomethyl)-3,8-di-o-tolyl-2,7-dioxaspiro[4.4]nonan-1-one

: 3,8-bis(bromomethyl)-3,8-di-o-tolyl-2,7-dioxaspiro[4.4]nonan-1-one

Guidance literature:: Multi-step reaction with 3 steps

1: pyridinium chlorochromate / dichloromethane / Molecular sieve

2: sodium dihydrogenphosphate; sodium chlorite / tert-butyl alcohol; water / 2 h

3: N-Bromosuccinimide; triphenylphosphine sulfide / dichloromethane / 12 h / -50 °C / Darkness

With sodium chlorite; sodium dihydrogenphosphate; N-Bromosuccinimide; triphenylphosphine sulfide; pyridinium chlorochromate; In dichloromethane; water; tert-butyl alcohol;
DOI:10.1002/anie.201310136

Reference yield:

: 445235-57-4
1-(3-bromoprop-1-en-2-yl)-2-methylbenzene

: 1643718-43-7
(3S,5R,8S)-3,8-bis(bromomethyl)-3,8-di-o-tolyl-2,7-dioxaspiro[4.4]nonan-1-one

: 3,8-bis(bromomethyl)-3,8-di-o-tolyl-2,7-dioxaspiro[4.4]nonan-1-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 0 - 25 °C / Inert atmosphere

1.2: 12 h / Inert atmosphere; Reflux

2.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 25 °C / Inert atmosphere

3.1: N-bromophthalimide; C₃₂H₃₉N₃O₃S / chloroform; hexane / 12 h / -60 °C / Inert atmosphere; Molecular sieve; Darkness

4.1: pyridinium chlorochromate / dichloromethane / Molecular sieve

5.1: sodium dihydrogenphosphate; sodium chlorite / tert-butyl alcohol; water / 2 h

6.1: N-Bromosuccinimide; triphenylphosphine sulfide / dichloromethane / 12 h / -50 °C / Darkness

With sodium chlorite; sodium dihydrogenphosphate; N-Bromosuccinimide; lithium aluminium tetrahydride; N-bromophthalimide; C₃₂H₃₉N₃O₃S; sodium hydride; triphenylphosphine sulfide; pyridinium chlorochromate; In tetrahydrofuran; hexane; dichloromethane; chloroform; water; mineral oil; tert-butyl alcohol;
DOI:10.1002/anie.201310136