(+/-)-1-(2-iodophenyl)-3-methylbut-3-en-2-ol

Base Information

• Chemical Name: (+/-)-1-(2-iodophenyl)-3-methylbut-3-en-2-ol
• CAS No.: 1177416-63-5
• Molecular Formula: C₁₁H₁₃IO
• Molecular Weight: 288.128
• Mol file: 1177416-63-5.mol

Synonyms:(+/-)-1-(2-iodophenyl)-3-methylbut-3-en-2-ol

Chemical Property of (+/-)-1-(2-iodophenyl)-3-methylbut-3-en-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-1-(2-iodophenyl)-3-methylbut-3-en-2-ol

There total 5 articles about (+/-)-1-(2-iodophenyl)-3-methylbut-3-en-2-ol 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: 83.0%

C11H13IO (1177416-79-3) → (+/-)-1-(2-iodophenyl)-3-methylbut-3-en-2-ol (1177416-63-5)

Guidance literature:

C₁₁H₁₃IO; With aluminum isopropoxide; In toluene; for 12h; Inert atmosphere; Reflux;

With hydrogenchloride; water; In diethyl ether; toluene; at 20 ℃; Inert atmosphere;

DOI:10.1016/j.tet.2009.05.020

Reference yield:

C11H11IO → (+/-)-1-(2-iodophenyl)-3-methylbut-3-en-2-ol (1177416-63-5)

Guidance literature:

With sodium tetrahydroborate; cerium(III) chloride heptahydrate; In methanol; at 0 ℃; for 0.166667h; Inert atmosphere;

DOI:10.1021/acs.orglett.6b02665

Reference yield:

phenylacetic acid (103-82-2) → (+/-)-1-(2-iodophenyl)-3-methylbut-3-en-2-ol (1177416-63-5)

Guidance literature:

Multi-step reaction with 4 steps

1: palladium diacetate; [bis(acetoxy)iodo]benzene; iodine / N,N-dimethyl-formamide / 24 h / 60 °C / Inert atmosphere

2: 1,1'-carbonyldiimidazole; triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

3: tetrahydrofuran / 0.17 h / 0 °C / Inert atmosphere

4: cerium(III) chloride heptahydrate; sodium tetrahydroborate / methanol / 0.17 h / 0 °C / Inert atmosphere

With sodium tetrahydroborate; [bis(acetoxy)iodo]benzene; cerium(III) chloride heptahydrate; iodine; palladium diacetate; triethylamine; 1,1'-carbonyldiimidazole; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 2: |Weinreb Ketone Synthesis / 4: |Luche Cerium Reduction;

DOI:10.1021/acs.orglett.6b02665

upstream raw materials:

C₁₁H₁₃IO

2-(2-iodophenyl)-N-methoxy-N-methylacetamide

phenylacetic acid

o-iodophenylacetic acid

Downstream raw materials:

(E)-ethyl 6-(2-iodophenyl)-4-methylhex-4-enoate

Refernces

• 1、 Pattenden, Gerald,Stoker, Davey A.,Winne, Johan M.. "A synthetic approach to C-nor-D-homosteroids based on a cascade of radical cyclisations from a vinylcyclopropane-substituted acyl radical precursor". experimental part. p. 5767 - 5775. Retrieved 2009/12/01.