5-benzyloxy-1-bromo-4-iodo-1,1,2,2-tetrafluoropentane

Base Information

• Chemical Name: 5-benzyloxy-1-bromo-4-iodo-1,1,2,2-tetrafluoropentane
• CAS No.: 1050610-45-1
• Molecular Formula: C₁₂H₁₂BrF₄IO
• Molecular Weight: 455.029
• Mol file: 1050610-45-1.mol

Synonyms:5-benzyloxy-1-bromo-4-iodo-1,1,2,2-tetrafluoropentane

Chemical Property of 5-benzyloxy-1-bromo-4-iodo-1,1,2,2-tetrafluoropentane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-benzyloxy-1-bromo-4-iodo-1,1,2,2-tetrafluoropentane

There total 1 articles about 5-benzyloxy-1-bromo-4-iodo-1,1,2,2-tetrafluoropentane 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: 95.0%

1-bromo-2-iodo-1,1,2,2-tetrafluoroethane (421-70-5) + benzyl allyl ether (14593-43-2) → 5-benzyloxy-1-bromo-4-iodo-1,1,2,2-tetrafluoropentane (1050610-45-1)

Guidance literature:

benzyl allyl ether; In water; acetonitrile; for 0.25h; Sonication; Inert atmosphere;

1-bromo-2-iodo-1,1,2,2-tetrafluoroethane; With sodium dithionite; sodium hydrogencarbonate; In water; acetonitrile; at 0 - 6 ℃; for 21h; Inert atmosphere;

DOI:10.1021/acs.joc.6b00302

Reference yield: 99.0%

5-benzyloxy-1-bromo-4-iodo-1,1,2,2-tetrafluoropentane (1050610-45-1) → (E)-5-benzyloxy-1-bromo-1,1,2,2-tetrafluoropent-3-ene (1050610-51-9)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; at -55 - -50 ℃; for 3h;

DOI:10.1021/acs.joc.6b00302

Reference yield:

5-benzyloxy-1-bromo-4-iodo-1,1,2,2-tetrafluoropentane (1050610-45-1) → (3R,4R)-5-benzyloxy-1-bromo-1,1,2,2-tetrafluoropentane-3,4-diol (1050610-71-3) + 5-benzyloxy-1-bromo-1,1,2,2-tetrafluoropentan-3-one + (3R,4R)-5-benzyloxy-1-bromo-3-hydroxy-1,1,2,2-tetrafluoropentan-4-yl formate

Guidance literature:

Multi-step reaction with 4 steps

1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 3 h / -55 - -50 °C

2.1: (DHQ)₂AQN; potassium hexacyanoferrate(III); potassium carbonate; potassium osmate; methanesulfonamide / water; tert-butyl alcohol / 216 h / 0 - 6 °C

3.1: triethylamine; thionyl chloride / dichloromethane / 0.57 h / 0 °C

3.2: 16 h / 0 - 20 °C

4.1: ammonium formate / N,N-dimethyl-formamide / 4 h / 80 °C

4.2: 0.5 h / 20 °C

With potassium osmate; thionyl chloride; methanesulfonamide; (DHQ)₂AQN; ammonium formate; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; potassium hexacyanoferrate(III); In dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1021/acs.joc.6b00302

upstream raw materials:

1-bromo-2-iodo-1,1,2,2-tetrafluoroethane

benzyl allyl ether

Downstream raw materials:

(E)-5-benzyloxy-1-bromo-1,1,2,2-tetrafluoropent-3-ene

(3R,4R)-5-benzyloxy-1-bromo-1,1,2,2-tetrafluoropentane-3,4-diol

Refernces

• 1、 Timofte, Roxana S.,Lindau, Bruno. "Enantioselective synthesis of tetrafluorinated glucose and galactose". supporting information; experimental part. p. 3673 - 3676. Retrieved 2009/07/01.