4-(3-chloro-1-phenyl-propoxy)-5-fluoro-benzo[b]thiophene

Base Information

• Chemical Name: 4-(3-chloro-1-phenyl-propoxy)-5-fluoro-benzo[b]thiophene
• CAS No.: 476199-74-3
• Molecular Formula: C₁₇H₁₄ClFOS
• Molecular Weight: 320.815
• Mol file: 476199-74-3.mol

Synonyms:

Chemical Property of 4-(3-chloro-1-phenyl-propoxy)-5-fluoro-benzo[b]thiophene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-(3-chloro-1-phenyl-propoxy)-5-fluoro-benzo[b]thiophene

There total 7 articles about 4-(3-chloro-1-phenyl-propoxy)-5-fluoro-benzo[b]thiophene 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-fluorosalicylaldehyde (394-50-3) → 4-(3-chloro-1-phenyl-propoxy)-5-fluoro-benzo[b]thiophene (476199-74-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 100 percent / K₂CO₃ / acetone

2: 78 percent / H₄NOAc / toluene

3: 94 percent / aq. NaOH

4: 67 percent / I₂ / 1,2-dimethoxy-ethane / 120 °C / microwave irradiation

5: 23 percent / DBU; DMA / 200 °C / microwave irradiation

6: BBr₃ / CH₂Cl₂

7: (4,4-dimethyl-1,1-dioxido-1,2,5-thiadiazolidin-2-yl)-Ph₃P⁺ / tetrahydrofuran

With sodium hydroxide; (4,4-dimethyl-1,1-dioxido-1,2,5-thiadiazolidin-2-yl)-Ph₃P⁺; ammonium acetate; iodine; boron tribromide; 2,4-dichlorophenoxyacetic acid dimethylamine; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; acetone; toluene; 7: Mitsunobu reaction;

DOI:10.1016/j.bmcl.2004.08.005

Reference yield:

fluoro-3 methoxy-2 benzaldehhyde (74266-68-5) → 4-(3-chloro-1-phenyl-propoxy)-5-fluoro-benzo[b]thiophene (476199-74-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 78 percent / H₄NOAc / toluene

2: 94 percent / aq. NaOH

3: 67 percent / I₂ / 1,2-dimethoxy-ethane / 120 °C / microwave irradiation

4: 23 percent / DBU; DMA / 200 °C / microwave irradiation

5: BBr₃ / CH₂Cl₂

6: (4,4-dimethyl-1,1-dioxido-1,2,5-thiadiazolidin-2-yl)-Ph₃P⁺ / tetrahydrofuran

With sodium hydroxide; (4,4-dimethyl-1,1-dioxido-1,2,5-thiadiazolidin-2-yl)-Ph₃P⁺; ammonium acetate; iodine; boron tribromide; 2,4-dichlorophenoxyacetic acid dimethylamine; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; toluene; 6: Mitsunobu reaction;

DOI:10.1016/j.bmcl.2004.08.005

Reference yield:

5-fluoro-4-methoxy-1-benzothiophene (476198-96-6) → 4-(3-chloro-1-phenyl-propoxy)-5-fluoro-benzo[b]thiophene (476199-74-3)

Guidance literature:

Multi-step reaction with 2 steps

1: BBr₃ / CH₂Cl₂

2: (4,4-dimethyl-1,1-dioxido-1,2,5-thiadiazolidin-2-yl)-Ph₃P⁺ / tetrahydrofuran

With (4,4-dimethyl-1,1-dioxido-1,2,5-thiadiazolidin-2-yl)-Ph₃P⁺; boron tribromide; In tetrahydrofuran; dichloromethane; 2: Mitsunobu reaction;

DOI:10.1016/j.bmcl.2004.08.005

upstream raw materials:

3-chloro-1-phenylpropanol

5-fluoro-4-hydroxybenzothiophene

3-fluorosalicylaldehyde

fluoro-3 methoxy-2 benzaldehhyde