6-Oxabicyclo[3.2.1]oct-2-ene, 2-(bromomethyl)-8,8-dimethyl-, (1R)-

Base Information

• Chemical Name: 6-Oxabicyclo[3.2.1]oct-2-ene, 2-(bromomethyl)-8,8-dimethyl-, (1R)-
• CAS No.: 105996-78-9
• Molecular Formula: C10H15BrO
• Molecular Weight: 231.132
• Mol file: 105996-78-9.mol

Synonyms:

Chemical Property of 6-Oxabicyclo[3.2.1]oct-2-ene, 2-(bromomethyl)-8,8-dimethyl-, (1R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 6-Oxabicyclo[3.2.1]oct-2-ene, 2-(bromomethyl)-8,8-dimethyl-, (1R)-

There total 1 articles about 6-Oxabicyclo[3.2.1]oct-2-ene, 2-(bromomethyl)-8,8-dimethyl-, (1R)- 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:

2,2-dimethyl-1,3-cyclohexanedione (562-13-0) → (1R,5R)-2-Bromomethyl-8,8-dimethyl-6-oxa-bicyclo[3.2.1]oct-2-ene (105996-78-9)

Guidance literature:

Multi-step reaction with 14 steps

1: 79 percent / H₂O / 48 h / 30 °C / fermentation, baker's yeast

2: p-TsOH / CH₂Cl₂ / 0.5 h / Ambient temperature

3: 1.) NaOMe / 1.)THF, benzene, 10 min, 6 deg C 2.) RT, overnight

4: 6.9 g / p-TsOH / benzene / 3.5 h / Heating

5: p-TsOH / CH₂Cl₂ / Ambient temperature

6: 19.5 g / NaBH₄ / tetrahydrofuran; ethanol / 1.5 h / 0 - 4 °C

7: 14.1 g / CdCO₃, HgCl₂ / aq. ethanol / 0.03 h / Heating

8: 66 percent / NaBH₄ / aq. ethanol; tetrahydrofuran / 1 h / 0 - 5 °C

9: 1.) (n-Bu)3SnCH₂I 2.) n-BuLi / 1.) THF,DMF,44 h, RT 2.) THF, n-hexane, 1 h -65 deg C

10: pyridine / Ambient temperature

11: 95.7 percent / pTsOH / methanol / 1.33 h / Ambient temperature

12: 90.7 percent / 4-(N,N-dimethylamino)pyridine / pyridine / 60 h / Ambient temperature

13: 86.8 percent / NaOMe / methanol / 24 h / Ambient temperature

14: C₅H₅NHBr₃

With dmap; sodium tetrahydroborate; n-butyllithium; cadmium(II) carbonate; sodium methylate; tri-n-butylstannylmethyl iodide; toluene-4-sulfonic acid; pyridinium hydrobromide perbromide; mercury dichloride; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; water; benzene;

DOI:10.1016/S0040-4020(01)91348-1

upstream raw materials:

2,2-dimethyl-1,3-cyclohexanedione