5-bromomethyl-4-(tert-butyldimethylsiloxy)-2-(3,4-dimethoxybenzyl)-6-methoxyisoindolin-1-one

Base Information

• Chemical Name: 5-bromomethyl-4-(tert-butyldimethylsiloxy)-2-(3,4-dimethoxybenzyl)-6-methoxyisoindolin-1-one
• CAS No.: 1236125-34-0
• Molecular Formula: C₂₅H₃₄BrNO₅Si
• Molecular Weight: 536.538

Synonyms:5-bromomethyl-4-(tert-butyldimethylsiloxy)-2-(3,4-dimethoxybenzyl)-6-methoxyisoindolin-1-one

Chemical Property of 5-bromomethyl-4-(tert-butyldimethylsiloxy)-2-(3,4-dimethoxybenzyl)-6-methoxyisoindolin-1-one

Chemical Property:

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Technology Process of 5-bromomethyl-4-(tert-butyldimethylsiloxy)-2-(3,4-dimethoxybenzyl)-6-methoxyisoindolin-1-one

There total 13 articles about 5-bromomethyl-4-(tert-butyldimethylsiloxy)-2-(3,4-dimethoxybenzyl)-6-methoxyisoindolin-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:

methyl 8-aminomethyl-5-methoxy-2,2-dimethyl-4H-benzo[d][1,3]dioxine-7carboxylate hydrochloride salt (1310461-17-6) → 5-bromomethyl-4-(tert-butyldimethylsiloxy)-2-(3,4-dimethoxybenzyl)-6-methoxyisoindolin-1-one (1236125-34-0)

Guidance literature:

Multi-step reaction with 6 steps

1: sodium methylate / methanol / 1 h / 20 °C

2: sodium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

3: hydrogenchloride / tetrahydrofuran; water / 20 °C

4: 1H-imidazole / N,N-dimethyl-formamide / 24 h / 20 °C

5: hydrogen fluoride / water; acetonitrile / 0 °C

6: carbon tetrabromide; triphenylphosphine / dichloromethane

With 1H-imidazole; hydrogenchloride; carbon tetrabromide; hydrogen fluoride; sodium methylate; sodium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/ejoc.201100173

Reference yield:

5-methoxy-2,2-dimethyl-8,9-dihydro-[1,3]dioxino[4,5-e]isoindol-7(4H)-one (1236125-62-4) → 5-bromomethyl-4-(tert-butyldimethylsiloxy)-2-(3,4-dimethoxybenzyl)-6-methoxyisoindolin-1-one (1236125-34-0)

Guidance literature:

Multi-step reaction with 5 steps

1: sodium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

2: hydrogenchloride / tetrahydrofuran; water / 20 °C

3: 1H-imidazole / N,N-dimethyl-formamide / 24 h / 20 °C

4: hydrogen fluoride / water; acetonitrile / 0 °C

5: carbon tetrabromide; triphenylphosphine / dichloromethane

With 1H-imidazole; hydrogenchloride; carbon tetrabromide; hydrogen fluoride; sodium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide; triphenylphosphine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/ejoc.201100173

Reference yield:

2-(3,4-dimethoxybenzyl)-4-hydroxy-5-hydroxymethyl-6-methoxyisoindolin-1-one (1310461-64-3) → 5-bromomethyl-4-(tert-butyldimethylsiloxy)-2-(3,4-dimethoxybenzyl)-6-methoxyisoindolin-1-one (1236125-34-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 1H-imidazole / N,N-dimethyl-formamide / 24 h / 20 °C

2: hydrogen fluoride / water; acetonitrile / 0 °C

3: carbon tetrabromide; triphenylphosphine / dichloromethane

With 1H-imidazole; carbon tetrabromide; hydrogen fluoride; triphenylphosphine; In dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/ejoc.201100173

upstream raw materials:

methyl 8-aminomethyl-5-methoxy-2,2-dimethyl-4H-benzo[d][1,3]dioxine-7carboxylate hydrochloride salt

5-methoxy-2,2-dimethyl-8,9-dihydro-[1,3]dioxino[4,5-e]isoindol-7(4H)-one

8-(3,4-dimethoxybenzyl)-2,2-dimethyl-8,9-dihydro-[1,3]dioxino[4,5-e]isoindol-7(4H)-one

2-(3,4-dimethoxybenzyl)-4-hydroxy-5-hydroxymethyl-6-methoxyisoindolin-1-one

Downstream raw materials:

4-(tert-butyldimethylsiloxy)-2-(3,4-dimethoxybenzyl)-6-methoxy-5-{[(4a'S,5'S,8a'S)-5',8a'-dimethyl-6'-oxooctahydro-2'H-spiro[[1,3]dioxolane-2,1'-naphthalene]-5'-yl]methyl}-isoindolin-1-one

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