1-bromo-4-phenyl-6-(trimethylsilyloxy)-5,6,8,9-tetrahydrobenzocyclohepten-7-one

Base Information

• Chemical Name: 1-bromo-4-phenyl-6-(trimethylsilyloxy)-5,6,8,9-tetrahydrobenzocyclohepten-7-one
• CAS No.: 1338797-06-0
• Molecular Formula: C₂₀H₂₃BrO₂Si
• Molecular Weight: 403.391

Synonyms:1-bromo-4-phenyl-6-(trimethylsilyloxy)-5,6,8,9-tetrahydrobenzocyclohepten-7-one

Chemical Property of 1-bromo-4-phenyl-6-(trimethylsilyloxy)-5,6,8,9-tetrahydrobenzocyclohepten-7-one

Chemical Property:

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Technology Process of 1-bromo-4-phenyl-6-(trimethylsilyloxy)-5,6,8,9-tetrahydrobenzocyclohepten-7-one

There total 8 articles about 1-bromo-4-phenyl-6-(trimethylsilyloxy)-5,6,8,9-tetrahydrobenzocyclohepten-7-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:

trimethylsilyl trifluoromethanesulfonate (27607-77-8) + 1-bromo-4-phenyl-5,6,8,9-tetrahydrobenzocyclohepten-7-one (1338796-89-6) → 4-bromo-1-phenyl-6-(trimethylsilyloxy)-5,6,8,9-tetrahydrobenzocyclohepten-7-one (1338797-05-9) + 1-bromo-4-phenyl-6-(trimethylsilyloxy)-5,6,8,9-tetrahydrobenzocyclohepten-7-one (1338797-06-0)

Guidance literature:

trimethylsilyl trifluoromethanesulfonate; 1-bromo-4-phenyl-5,6,8,9-tetrahydrobenzocyclohepten-7-one; With triethylamine; In toluene; at 80 ℃; for 4h; Inert atmosphere;

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 ℃; for 3h; Inert atmosphere;

DOI:10.1016/j.bmc.2011.06.089

Reference yield:

4-bromo-2,3-dimethylbenzenediazonium tetrafluoroborate → 4-bromo-1-phenyl-6-(trimethylsilyloxy)-5,6,8,9-tetrahydrobenzocyclohepten-7-one (1338797-05-9) + 1-bromo-4-phenyl-6-(trimethylsilyloxy)-5,6,8,9-tetrahydrobenzocyclohepten-7-one (1338797-06-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: palladium diacetate / methanol / 2 h / 65 °C / Inert atmosphere

2.1: N-Bromosuccinimide / tetrachloromethane / Irradiation

3.1: tetrabutylammomium bromide; sodium hydrogencarbonate / dichloromethane; water / 16 h / 40 °C / Inert atmosphere

4.1: sulfuric acid / water; acetonitrile / 72 h / 100 °C

5.1: triethylamine / toluene / 4 h / 80 °C / Inert atmosphere

5.2: 3 h / 0 °C / Inert atmosphere

With N-Bromosuccinimide; sulfuric acid; tetrabutylammomium bromide; palladium diacetate; sodium hydrogencarbonate; triethylamine; In methanol; tetrachloromethane; dichloromethane; water; toluene; acetonitrile;

DOI:10.1016/j.bmc.2011.06.089

Reference yield:

4-bromo-2,3-dimethyl-biphenyl (1338796-82-9) → 4-bromo-1-phenyl-6-(trimethylsilyloxy)-5,6,8,9-tetrahydrobenzocyclohepten-7-one (1338797-05-9) + 1-bromo-4-phenyl-6-(trimethylsilyloxy)-5,6,8,9-tetrahydrobenzocyclohepten-7-one (1338797-06-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: N-Bromosuccinimide / tetrachloromethane / Irradiation

2.1: tetrabutylammomium bromide; sodium hydrogencarbonate / dichloromethane; water / 16 h / 40 °C / Inert atmosphere

3.1: sulfuric acid / water; acetonitrile / 72 h / 100 °C

4.1: triethylamine / toluene / 4 h / 80 °C / Inert atmosphere

4.2: 3 h / 0 °C / Inert atmosphere

With N-Bromosuccinimide; sulfuric acid; tetrabutylammomium bromide; sodium hydrogencarbonate; triethylamine; In tetrachloromethane; dichloromethane; water; toluene; acetonitrile;

DOI:10.1016/j.bmc.2011.06.089

upstream raw materials:

4-bromo-2,3-dimethyl-biphenyl

4-bromo-2,3-bis(bromomethyl)-biphenyl

4-bromo-2,3-dimethylaniline hydrobromide

dimethyl 1-bromo-4-phenyl-7-oxo-5,6,8,9-tetrahydro-benzocycloheptene-6,8-dicarboxylate

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