(2R)-tetrahydro-2-[(R)-bromo(4-trifluoromethoxyphenyl)methyl]furan

Base Information

• Chemical Name: (2R)-tetrahydro-2-[(R)-bromo(4-trifluoromethoxyphenyl)methyl]furan
• CAS No.: 1351858-81-5
• Molecular Formula: C₁₂H₁₂BrF₃O₂
• Molecular Weight: 325.125
• Mol file: 1351858-81-5.mol

Synonyms:(2R)-tetrahydro-2-[(R)-bromo(4-trifluoromethoxyphenyl)methyl]furan

Chemical Property of (2R)-tetrahydro-2-[(R)-bromo(4-trifluoromethoxyphenyl)methyl]furan

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R)-tetrahydro-2-[(R)-bromo(4-trifluoromethoxyphenyl)methyl]furan

There total 7 articles about (2R)-tetrahydro-2-[(R)-bromo(4-trifluoromethoxyphenyl)methyl]furan 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:

(4Z)-5-(4-trifluoromethoxyphenyl)-4-penten-1-ol (1351858-70-2) → (2S)-tetrahydro-2-[(S)-bromo(4-trifluoromethoxyphenyl)methyl]furan + (2R)-tetrahydro-2-[(R)-bromo(4-trifluoromethoxyphenyl)methyl]furan (1351858-81-5)

Guidance literature:

With (R)-3,3'-bis(2,4,6-triisopropylphenyl)-1,1'-binaphthyl-2,2'-diylhydrogenphosphate; N-Bromosuccinimide; triphenylphosphine sulfide; In toluene; at 0 ℃; for 12h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1021/ol203033k

Reference yield:

(4Z)-5-(4-trifluoromethoxyphenyl)-4-pentenenitrile (1351858-94-0) → (2S)-tetrahydro-2-[(S)-bromo(4-trifluoromethoxyphenyl)methyl]furan + (2R)-tetrahydro-2-[(R)-bromo(4-trifluoromethoxyphenyl)methyl]furan (1351858-81-5)

Guidance literature:

Multi-step reaction with 3 steps

1: water; sodium hydroxide / 24 h / Reflux

2: lithium aluminium tetrahydride / tetrahydrofuran / 1.5 h / 0 °C

3: (R)-3,3'-bis(2,4,6-triisopropylphenyl)-1,1'-binaphthyl-2,2'-diylhydrogenphosphate; N-Bromosuccinimide; triphenylphosphine sulfide / toluene / 12 h / 0 °C / Inert atmosphere

With (R)-3,3'-bis(2,4,6-triisopropylphenyl)-1,1'-binaphthyl-2,2'-diylhydrogenphosphate; N-Bromosuccinimide; lithium aluminium tetrahydride; water; triphenylphosphine sulfide; sodium hydroxide; In tetrahydrofuran; toluene;

DOI:10.1021/ol203033k

Reference yield:

(Z)-5-[(4-trifluoromethoxy)phenyl]pent-4-enoic acid (1351858-99-5) → (2S)-tetrahydro-2-[(S)-bromo(4-trifluoromethoxyphenyl)methyl]furan + (2R)-tetrahydro-2-[(R)-bromo(4-trifluoromethoxyphenyl)methyl]furan (1351858-81-5)

Guidance literature:

Multi-step reaction with 2 steps

1: lithium aluminium tetrahydride / tetrahydrofuran / 1.5 h / 0 °C

2: (R)-3,3'-bis(2,4,6-triisopropylphenyl)-1,1'-binaphthyl-2,2'-diylhydrogenphosphate; N-Bromosuccinimide; triphenylphosphine sulfide / toluene / 12 h / 0 °C / Inert atmosphere

With (R)-3,3'-bis(2,4,6-triisopropylphenyl)-1,1'-binaphthyl-2,2'-diylhydrogenphosphate; N-Bromosuccinimide; lithium aluminium tetrahydride; triphenylphosphine sulfide; In tetrahydrofuran; toluene;

DOI:10.1021/ol203033k

upstream raw materials:

(4Z)-5-(4-trifluoromethoxyphenyl)-4-penten-1-ol

(4Z)-5-(4-trifluoromethoxyphenyl)-4-pentenenitrile

(Z)-5-[(4-trifluoromethoxy)phenyl]pent-4-enoic acid

p-trifluoromethoxybenzaldehyde