1-((4-fluorophenyl)ethynyl)-3,3-bis(trifluoromethyl)-1,3-dihydro-1λ³-benzo[d][1,2]iodaoxole

Base Information

• Chemical Name: 1-((4-fluorophenyl)ethynyl)-3,3-bis(trifluoromethyl)-1,3-dihydro-1λ³-benzo[d][1,2]iodaoxole
• CAS No.: 1620093-17-5
• Molecular Formula: C₁₇H₈F₇IO
• Molecular Weight: 488.143

Synonyms:1-((4-fluorophenyl)ethynyl)-3,3-bis(trifluoromethyl)-1,3-dihydro-1λ³-benzo[d][1,2]iodaoxole

Chemical Property of 1-((4-fluorophenyl)ethynyl)-3,3-bis(trifluoromethyl)-1,3-dihydro-1λ³-benzo[d][1,2]iodaoxole

Chemical Property:

Purity/Quality:

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Technology Process of 1-((4-fluorophenyl)ethynyl)-3,3-bis(trifluoromethyl)-1,3-dihydro-1λ³-benzo[d][1,2]iodaoxole

There total 5 articles about 1-((4-fluorophenyl)ethynyl)-3,3-bis(trifluoromethyl)-1,3-dihydro-1λ³-benzo[d][1,2]iodaoxole 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:

3,3-bis(trifluoromethyl)-1λ3 -benzo[d][1,2]iodaoxol-1(3H)-yl acetate + 1-(4-fluorophenyl)-2-trimethylsilylacetylene (130995-12-9) → 1-((4-fluorophenyl)ethynyl)-3,3-bis(trifluoromethyl)-1,3-dihydro-1λ3-benzo[d][1,2]iodaoxole (1620093-17-5)

Guidance literature:

3,3-bis(trifluoromethyl)-1λ³ -benzo[d][1,2]iodaoxol-1(3H)-yl acetate; With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 20 ℃; for 1h;

1-(4-fluorophenyl)-2-trimethylsilylacetylene; In dichloromethane; at 20 ℃; for 18h;

DOI:10.1039/c4ob00969j

Reference yield:

1-(4-fluorophenyl)-2-trimethylsilylacetylene (130995-12-9) + 3,3-bis(trifluoromethyl)-1λ3-benzo[d][1,2]iodaoxol-1(3H)-ol → 1-((4-fluorophenyl)ethynyl)-3,3-bis(trifluoromethyl)-1,3-dihydro-1λ3-benzo[d][1,2]iodaoxole (1620093-17-5)

Guidance literature:

3,3-bis(trifluoromethyl)-1λ³-benzo[d][1,2]iodaoxol-1(3H)-ol; With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 20 ℃; for 0.5h; Inert atmosphere;

1-(4-fluorophenyl)-2-trimethylsilylacetylene; In acetonitrile; at 0 - 20 ℃; for 12h;

With pyridine; at 20 ℃; for 3h;

DOI:10.1021/acs.orglett.1c03667

Reference yield:

1,1,1,3,3,3-hexafluoro-2-phenylisopropyl alcohol (718-64-9) → 1-((4-fluorophenyl)ethynyl)-3,3-bis(trifluoromethyl)-1,3-dihydro-1λ3-benzo[d][1,2]iodaoxole (1620093-17-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: n-butyllithium; N,N,N,N,-tetramethylethylenediamine / tetrahydrofuran; hexane / 0 - 20 °C / Inert atmosphere

1.2: 4 h / 0 - 20 °C / Inert atmosphere

2.1: tert-butylhypochlorite / dichloromethane / 0.5 h / 0 - 20 °C

3.1: N-benzyl-N,N,N-triethylammonium chloride; potassium hydroxide / dichloromethane; water / 12 h / 20 °C

4.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

4.2: 12 h / 0 - 20 °C

4.3: 3 h / 20 °C

With n-butyllithium; tert-butylhypochlorite; N,N,N,N,-tetramethylethylenediamine; trimethylsilyl trifluoromethanesulfonate; N-benzyl-N,N,N-triethylammonium chloride; potassium hydroxide; In tetrahydrofuran; hexane; dichloromethane; water;

DOI:10.1021/acs.orglett.1c03667

upstream raw materials:

1-(4-fluorophenyl)-2-trimethylsilylacetylene

1,1,1,3,3,3-hexafluoro-2-phenylisopropyl alcohol

1,1,1,3,3,3-hexafluoro-2-(2-iodophenyl)-propan-2-ol

1-chloro-3,3-bis(trifluoromethyl)-1,3-dihydro-1λ³-benzo[d][1,2]iodaoxole

Downstream raw materials:

1-ethynyl-4-fluorobenzene

1,4-diphenyl-1,3-butadiyne

1,1,1,3,3,3-hexafluoro-2-(2-iodophenyl)-propan-2-ol

Triphenylphosphine oxide

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