4-bromo-5-(3-hydroxypropyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran-3-carbaldehyde

Base Information

• Chemical Name: 4-bromo-5-(3-hydroxypropyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran-3-carbaldehyde
• CAS No.: 144735-66-0
• Molecular Formula: C₂₀H₁₉BrO₆
• Molecular Weight: 435.271
• Mol file: 144735-66-0.mol

Synonyms:4-bromo-5-(3-hydroxypropyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran-3-carbaldehyde

Chemical Property of 4-bromo-5-(3-hydroxypropyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran-3-carbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-bromo-5-(3-hydroxypropyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran-3-carbaldehyde

There total 16 articles about 4-bromo-5-(3-hydroxypropyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran-3-carbaldehyde 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:

vanillin (121-33-5,8014-42-4) → 4-bromo-5-(3-hydroxypropyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran-3-carbaldehyde (144735-66-0)

Guidance literature:

Multi-step reaction with 9 steps

1: 82 percent / Br₂, HOAc / 1 h / Ambient temperature

2: 98 percent / pyrrolidine / pyridine / 6 h / 100 °C

3: 1) CuSO₄*H₂O, NH₄OH, NH₂OH*HCl, 2) pyridine / 1) THF, EtOH, 2) 115 deg C, 20 h

4: 72 percent / LiAlH₄ / tetrahydrofuran / 4 h / Ambient temperature

5: 80 percent / pyridine / 18 h / Ambient temperature

6: 1) KCl, HCl(g) / 1) Et₂O, 0 deg C, 2) EtOH, H₂O, 50 deg C

7: 87 percent / pyridine / 10 h / Ambient temperature

8: 1) NBS, AIBn, 2) n-BuNH₂ / 1) CCl₄, 95 deg C, 10 min, 2) RT, 10 min

9: 1N NaOH / methanol / 1 h / Ambient temperature

With pyrrolidine; pyridine; hydrogenchloride; ammonium hydroxide; sodium hydroxide; N-Bromosuccinimide; lithium aluminium tetrahydride; 2,2'-azobis(isobutyronitrile); potassium chloride; hydroxylamine hydrochloride; bromine; copper(II) sulfate; acetic acid; N-butylamine; In tetrahydrofuran; pyridine; methanol;

DOI:10.1021/jo00052a046

Reference yield:

4-benzyloxy-3-methoxyacetophenone (1835-11-6) → 4-bromo-5-(3-hydroxypropyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran-3-carbaldehyde (144735-66-0)

Guidance literature:

Multi-step reaction with 9 steps

1: 63 percent / POCl₃ / 1) 0 deg C, 20 min, 2) 65 deg C, 10 h

2: 79 percent / NaOH / H₂O; dioxane / 2 h / 80 °C

3: 1) CuSO₄*H₂O, NH₄OH, NH₂OH*HCl, 2) pyridine / 1) THF, EtOH, 2) 115 deg C, 20 h

4: 72 percent / LiAlH₄ / tetrahydrofuran / 4 h / Ambient temperature

5: 80 percent / pyridine / 18 h / Ambient temperature

6: 1) KCl, HCl(g) / 1) Et₂O, 0 deg C, 2) EtOH, H₂O, 50 deg C

7: 87 percent / pyridine / 10 h / Ambient temperature

8: 1) NBS, AIBn, 2) n-BuNH₂ / 1) CCl₄, 95 deg C, 10 min, 2) RT, 10 min

9: 1N NaOH / methanol / 1 h / Ambient temperature

With pyridine; hydrogenchloride; ammonium hydroxide; sodium hydroxide; N-Bromosuccinimide; lithium aluminium tetrahydride; 2,2'-azobis(isobutyronitrile); potassium chloride; hydroxylamine hydrochloride; copper(II) sulfate; N-butylamine; trichlorophosphate; In tetrahydrofuran; 1,4-dioxane; methanol; water;

DOI:10.1021/jo00052a046

Reference yield:

5-bromo-4-hydroxy-3-methoxybenzaldehyde (2973-76-4) → 4-bromo-5-(3-hydroxypropyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran-3-carbaldehyde (144735-66-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 98 percent / pyrrolidine / pyridine / 6 h / 100 °C

2: 1) CuSO₄*H₂O, NH₄OH, NH₂OH*HCl, 2) pyridine / 1) THF, EtOH, 2) 115 deg C, 20 h

3: 72 percent / LiAlH₄ / tetrahydrofuran / 4 h / Ambient temperature

4: 80 percent / pyridine / 18 h / Ambient temperature

5: 1) KCl, HCl(g) / 1) Et₂O, 0 deg C, 2) EtOH, H₂O, 50 deg C

6: 87 percent / pyridine / 10 h / Ambient temperature

7: 1) NBS, AIBn, 2) n-BuNH₂ / 1) CCl₄, 95 deg C, 10 min, 2) RT, 10 min

8: 1N NaOH / methanol / 1 h / Ambient temperature

With pyrrolidine; pyridine; hydrogenchloride; ammonium hydroxide; sodium hydroxide; N-Bromosuccinimide; lithium aluminium tetrahydride; 2,2'-azobis(isobutyronitrile); potassium chloride; hydroxylamine hydrochloride; copper(II) sulfate; N-butylamine; In tetrahydrofuran; pyridine; methanol;

DOI:10.1021/jo00052a046

upstream raw materials:

vanillin

4-benzyloxy-3-methoxyacetophenone

5-bromo-4-hydroxy-3-methoxybenzaldehyde

methyl 3-methoxy-4-hydroxy-5-bromocinnamate