2-(trimethylsilyl)-5-bromofuran

Base Information

• Chemical Name: 2-(trimethylsilyl)-5-bromofuran
• CAS No.: 119987-27-8
• Molecular Formula: C₇H₁₁BrOSi
• Molecular Weight: 219.153
• Mol file: 119987-27-8.mol

Synonyms:2-(trimethylsilyl)-5-bromofuran

Chemical Property of 2-(trimethylsilyl)-5-bromofuran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(trimethylsilyl)-5-bromofuran

There total 1 articles about 2-(trimethylsilyl)-5-bromofuran 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: 71.0%

2,5-dibromofuran (32460-00-7) + chloro-trimethyl-silane (75-77-4) → 2-furyltrimethylsilane (1578-33-2) + 2,5-bis(trimethylsilyl)-furane (1578-29-6) + 2-(trimethylsilyl)-5-bromofuran (119987-27-8)

Guidance literature:

With tetrabutylammomium bromide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; Yields of byproduct given; electrochemical conditions (Al anode, 2.2 F_.mol^-1);

DOI:10.1016/S0022-328X(98)00853-5

Reference yield:

2-trimethylsilyl-4-bromofuran (119987-27-8) → 2-trimethylsilyl-4-<(3E,7E)-10-(2,6,6-trimethyl-1-cyclohexen-1-yl)-8-methyl-4-formyl-1-hydroxy-3,7-decadien-1-yl>-furan (110202-12-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 78 percent / s-butyllithium / diethyl ether; cyclohexane / 1 h / Ambient temperature

2: 84 percent / BF₃*Et₂O / CHCl₃ / 7 h / Ambient temperature

3: n-butyllithium / tetrahydrofuran; various solvent(s) / 12 h / -80 °C

4: HgCl₂, CaCO₃ / acetonitrile; H₂O / 4 h / Heating

5: NaBH₄ / ethanol / 2 h / Ambient temperature

6: 42 percent / tetra-n-propylammmonium perruthenate, crushed 4 Angstroem molecular sieves, N-methylmorpholine N-oxide / CH₂Cl₂; acetonitrile / 3 h / Ambient temperature

With sodium tetrahydroborate; n-butyllithium; tetrapropylammonium perruthennate; 4 A molecular sieve; boron trifluoride diethyl etherate; sec.-butyllithium; 4-methylmorpholine N-oxide; calcium carbonate; mercury dichloride; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; chloroform; cyclohexane; water; acetonitrile;

DOI:10.1016/S0040-4020(01)85353-9

Reference yield:

2-trimethylsilyl-4-bromofuran (119987-27-8) → 2-trimethylsilyl-4-<(2E,6E)-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-7-methyl-4-hydroxymethyl-1-hydroxy-2,6-nonadien-1-yl>-furan (160084-18-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 78 percent / s-butyllithium / diethyl ether; cyclohexane / 1 h / Ambient temperature

2: 84 percent / BF₃*Et₂O / CHCl₃ / 7 h / Ambient temperature

3: n-butyllithium / tetrahydrofuran; various solvent(s) / 12 h / -80 °C

4: HgCl₂, CaCO₃ / acetonitrile; H₂O / 4 h / Heating

5: NaBH₄ / ethanol / 2 h / Ambient temperature

With sodium tetrahydroborate; n-butyllithium; boron trifluoride diethyl etherate; sec.-butyllithium; calcium carbonate; mercury dichloride; In tetrahydrofuran; diethyl ether; ethanol; chloroform; cyclohexane; water; acetonitrile;

DOI:10.1016/S0040-4020(01)85353-9

upstream raw materials:

2,5-dibromofuran

chloro-trimethyl-silane

Downstream raw materials:

2-trimethylsilyl-4-<(3E,7E)-10-(2,6,6-trimethyl-1-cyclohexen-1-yl)-8-methyl-4-formyl-1-hydroxy-3,7-decadien-1-yl>-furan

2-trimethylsilyl-4-<(2E,6E)-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-7-methyl-4-hydroxymethyl-1-hydroxy-2,6-nonadien-1-yl>-furan

2-<(2E,6E)-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-7-methyl-3-<(tert-butyldimethylsilyloxy)methyl>-2,6-nonadienyl>-2-<2-trimethylsilylfuran-4-yl>-1,3-dithian

Refernces