(+/-)-2-bromo-1-<(E)-4-t-butyldimethylsilyloxy-1-heptenyl>-3,4,5-trimethoxybenzene

Base Information

Chemical Name:(+/-)-2-bromo-1-<(E)-4-t-butyldimethylsilyloxy-1-heptenyl>-3,4,5-trimethoxybenzene
CAS No.:123731-61-3
Molecular Formula:C₂₂H₃₇BrO₄Si
Molecular Weight:473.523
Hs Code.:

Synonyms:(+/-)-2-bromo-1-<(E)-4-t-butyldimethylsilyloxy-1-heptenyl>-3,4,5-trimethoxybenzene

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Chemical Property of (+/-)-2-bromo-1-<(E)-4-t-butyldimethylsilyloxy-1-heptenyl>-3,4,5-trimethoxybenzene

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Technology Process of (+/-)-2-bromo-1-<(E)-4-t-butyldimethylsilyloxy-1-heptenyl>-3,4,5-trimethoxybenzene

There total 13 articles about (+/-)-2-bromo-1-<(E)-4-t-butyldimethylsilyloxy-1-heptenyl>-3,4,5-trimethoxybenzene 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: 80.0%

: 123731-60-2,123755-45-3
Methanesulfonic acid 1-(2-bromo-3,4,5-trimethoxy-phenyl)-4-(tert-butyl-dimethyl-silanyloxy)-heptyl ester

: 123731-61-3
(+/-)-2-bromo-1-<(E)-4-t-butyldimethylsilyloxy-1-heptenyl>-3,4,5-trimethoxybenzene

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In benzene; for 2h; Heating;
DOI:10.1016/S0040-4020(01)80027-2

Reference yield:

: 2305-25-1
3-hydroxy-hexanoic acid ethyl ester

: 123731-61-3
(+/-)-2-bromo-1-<(E)-4-t-butyldimethylsilyloxy-1-heptenyl>-3,4,5-trimethoxybenzene

Guidance literature:: Multi-step reaction with 9 steps

1: 87 percent / imidazole / dimethylformamide / 15 h / Ambient temperature

2: 92 percent / 1.) lithium borohydride; 2.) lithium triethylborohydride / 1.) rt., ether; 2.) THF, 3h, reflux

3: pyridine / 3 h / 0 - 5 °C

4: 85 percent / NaI, NaHCO₃ / acetone / 2 h / Heating

5: 92 percent / n-BuLi / tetrahydrofuran; hexane / 2 h / -20 °C

6: sodium acetate, bromine / acetic acid / 2 h / Ambient temperature

7: 85 percent / NaOH / methanol / 1 h / Ambient temperature

8: triethylamin / tetrahydrofuran / 2 h / 0 °C

9: 80 percent / DBU / benzene / 2 h / Heating

With 1H-imidazole; sodium hydroxide; lithium borohydride; n-butyllithium; bromine; sodium acetate; lithium triethylborohydride; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; sodium iodide; In tetrahydrofuran; pyridine; methanol; hexane; acetic acid; N,N-dimethyl-formamide; acetone; benzene;
DOI:10.1016/S0040-4020(01)80027-2

Reference yield:

: 3840-31-1
(3,4,5-trimethoxyphenyl)methanol

: 123731-61-3
(+/-)-2-bromo-1-<(E)-4-t-butyldimethylsilyloxy-1-heptenyl>-3,4,5-trimethoxybenzene

Guidance literature:: Multi-step reaction with 7 steps

1: thionyl chloride / diethyl ether / 3 h / Heating

2: 83 percent / sodium hydride / dimethylformamide / 2 h / Ambient temperature

3: 92 percent / n-BuLi / tetrahydrofuran; hexane / 2 h / -20 °C

4: sodium acetate, bromine / acetic acid / 2 h / Ambient temperature

5: 85 percent / NaOH / methanol / 1 h / Ambient temperature

6: triethylamin / tetrahydrofuran / 2 h / 0 °C

7: 80 percent / DBU / benzene / 2 h / Heating

With sodium hydroxide; n-butyllithium; thionyl chloride; bromine; sodium acetate; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; methanol; diethyl ether; hexane; acetic acid; N,N-dimethyl-formamide; benzene;
DOI:10.1016/S0040-4020(01)80027-2