(R)-4-(4-bromophenyl)-6-(trifluoromethyl)-6-phenyl-5,6-dihydro-2H-pyran-2-one

Base Information

• Chemical Name: (R)-4-(4-bromophenyl)-6-(trifluoromethyl)-6-phenyl-5,6-dihydro-2H-pyran-2-one
• CAS No.: 1332645-29-0
• Molecular Formula: C₁₈H₁₂BrF₃O₂
• Molecular Weight: 397.191
• Mol file: 1332645-29-0.mol

Synonyms:(R)-4-(4-bromophenyl)-6-(trifluoromethyl)-6-phenyl-5,6-dihydro-2H-pyran-2-one

Chemical Property of (R)-4-(4-bromophenyl)-6-(trifluoromethyl)-6-phenyl-5,6-dihydro-2H-pyran-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-4-(4-bromophenyl)-6-(trifluoromethyl)-6-phenyl-5,6-dihydro-2H-pyran-2-one

There total 6 articles about (R)-4-(4-bromophenyl)-6-(trifluoromethyl)-6-phenyl-5,6-dihydro-2H-pyran-2-one 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: 91.0%

2,2,2-Trifluoroacetophenone (434-45-7) + 3-(4-bromophenyl)but-2-enoyl chloride → (R)-4-(4-bromophenyl)-6-(trifluoromethyl)-6-phenyl-5,6-dihydro-2H-pyran-2-one (1332645-29-0)

Guidance literature:

With BF₄*C₃₃H₄₂N₃OSi⁽¹⁺⁾; caesium carbonate; triethylamine; In tetrahydrofuran; at -78 ℃; for 8h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1002/adsc.201100178

Reference yield:

2,2,2-Trifluoroacetophenone (434-45-7) + 3-(4-bromophenyl)butanoic acid (53086-46-7) → (R)-4-(4-bromophenyl)-6-(trifluoromethyl)-6-phenyl-5,6-dihydro-2H-pyran-2-one (1332645-29-0) + (S)-4-(4-bromophenyl)-6-phenyl-6-(trifluoromethyl)-5,6-dihydro-2H-pyran-2-one

Guidance literature:

With (5aR,10bS)-2-mesityl-5a,10b-dihydro-4H,6H-indeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazin-2-ium tetrafluoroborate; 3,5,3',5'-tetra-tert-butyl-4,4'-diphenoquinone; caesium carbonate; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In tetrahydrofuran; at 25 ℃; for 12h; Overall yield = 72 %; Overall yield = 57 mg; enantioselective reaction; Inert atmosphere;

DOI:10.1021/acs.orglett.5b03223

Reference yield:

3-(4-bromophenyl)but-2-enoic acid ethyl ester (76346-17-3) → (R)-4-(4-bromophenyl)-6-(trifluoromethyl)-6-phenyl-5,6-dihydro-2H-pyran-2-one (1332645-29-0) + (S)-4-(4-bromophenyl)-6-phenyl-6-(trifluoromethyl)-5,6-dihydro-2H-pyran-2-one

Guidance literature:

Multi-step reaction with 3 steps

1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C

2: manganese(IV) oxide / chloroform / 20 - 60 °C

3: BF₄^(1-)*C₂₁H₂₂N₃O⁽¹⁺⁾; 3,5,3',5'-tetra-tert-butyl-4,4'-diphenoquinone; potassium carbonate; magnesium triflate; scandium tris(trifluoromethanesulfonate) / 48 h / 0 °C / Inert atmosphere

With manganese(IV) oxide; lithium aluminium tetrahydride; 3,5,3',5'-tetra-tert-butyl-4,4'-diphenoquinone; BF₄^(1-)*C₂₁H₂₂N₃O⁽¹⁺⁾; potassium carbonate; magnesium triflate; scandium tris(trifluoromethanesulfonate); In tetrahydrofuran; chloroform;

DOI:10.1021/ja303618z

upstream raw materials:

2,2,2-Trifluoroacetophenone

3-(p-bromophenyl)-but-2-enal

3-(4-bromophenyl)but-2-enoic acid ethyl ester

para-bromoacetophenone

Downstream raw materials:

C₁₈H₁₆BrF₃O₂

C₁₈H₁₂BrF₃O₃

C₂₀H₂₀BrF₃O₃

C₂₂H₂₁BrF₃NO₂