(4-Chloro-5-fluoro-3-methoxy-pyridin-2-yl)-cyclopropyl-acetaldehyde

Base Information

• Chemical Name: (4-Chloro-5-fluoro-3-methoxy-pyridin-2-yl)-cyclopropyl-acetaldehyde
• CAS No.: 1025973-54-9
• Molecular Formula: C₁₁H₁₁ClFNO₂
• Molecular Weight: 243.665
• Mol file: 1025973-54-9.mol

Synonyms:

Chemical Property of (4-Chloro-5-fluoro-3-methoxy-pyridin-2-yl)-cyclopropyl-acetaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4-Chloro-5-fluoro-3-methoxy-pyridin-2-yl)-cyclopropyl-acetaldehyde

There total 11 articles about (4-Chloro-5-fluoro-3-methoxy-pyridin-2-yl)-cyclopropyl-acetaldehyde 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-chloro-2,4,5,6-tetrafluoropyridine (1735-84-8) → (4-Chloro-5-fluoro-3-methoxy-pyridin-2-yl)-cyclopropyl-acetaldehyde (1025973-54-9)

Guidance literature:

Multi-step reaction with 11 steps

1: 53 percent / tetrahydrofuran / 16 h / Ambient temperature

2: 83 percent / H₂, Et₃N / 10percent Pd(OH)2/C / ethyl acetate / 18 h / 3040 Torr / Ambient temperature

3: 1.) LDA, 2.) (MeO)3B, 3.) aq. 30percent H₂O₂

4: 91 percent / DEAD, Ph₃P / tetrahydrofuran / 0.17 h / Ambient temperature

5: 1.) N₂H₄*H₂O, 2.) O₂, 20percent aq. NaOH / 1.) n-PrOH, reflux, 3 h, 2.) MeOH, 3 d

6: 1.) LDA / 1.) THF, -78 deg C, 15 min, 2.) THF, a) -78 deg C, 1 h, b) 0 deg C, 1 h

7: CF₃COOH / 1 h / Ambient temperature

8: POCl₃, DMF / CH₂Cl₂

9: aq. HCl / 3 h / 80 - 85 °C

10: LiAlH₄ / tetrahydrofuran / 1 h / Ambient temperature

11: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) CH₂Cl₂, from -78 deg C to -10 deg C, 15 min

With hydrogenchloride; sodium hydroxide; lithium aluminium tetrahydride; oxalyl dichloride; Trimethyl borate; hydrogen; dihydrogen peroxide; oxygen; hydrazine hydrate; dimethyl sulfoxide; triethylamine; N,N-dimethyl-formamide; triphenylphosphine; trifluoroacetic acid; lithium diisopropyl amide; diethylazodicarboxylate; trichlorophosphate; palladium dihydroxide; In tetrahydrofuran; dichloromethane; ethyl acetate;

DOI:10.1021/jm960207w

Reference yield:

4-tert-butoxy-3-chloro-2,5,6-trifluoropyridine (169749-81-9) → (4-Chloro-5-fluoro-3-methoxy-pyridin-2-yl)-cyclopropyl-acetaldehyde (1025973-54-9)

Guidance literature:

Multi-step reaction with 10 steps

1: 83 percent / H₂, Et₃N / 10percent Pd(OH)2/C / ethyl acetate / 18 h / 3040 Torr / Ambient temperature

2: 1.) LDA, 2.) (MeO)3B, 3.) aq. 30percent H₂O₂

3: 91 percent / DEAD, Ph₃P / tetrahydrofuran / 0.17 h / Ambient temperature

4: 1.) N₂H₄*H₂O, 2.) O₂, 20percent aq. NaOH / 1.) n-PrOH, reflux, 3 h, 2.) MeOH, 3 d

5: 1.) LDA / 1.) THF, -78 deg C, 15 min, 2.) THF, a) -78 deg C, 1 h, b) 0 deg C, 1 h

6: CF₃COOH / 1 h / Ambient temperature

7: POCl₃, DMF / CH₂Cl₂

8: aq. HCl / 3 h / 80 - 85 °C

9: LiAlH₄ / tetrahydrofuran / 1 h / Ambient temperature

10: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) CH₂Cl₂, from -78 deg C to -10 deg C, 15 min

With hydrogenchloride; sodium hydroxide; lithium aluminium tetrahydride; oxalyl dichloride; Trimethyl borate; hydrogen; dihydrogen peroxide; oxygen; hydrazine hydrate; dimethyl sulfoxide; triethylamine; N,N-dimethyl-formamide; triphenylphosphine; trifluoroacetic acid; lithium diisopropyl amide; diethylazodicarboxylate; trichlorophosphate; palladium dihydroxide; In tetrahydrofuran; dichloromethane; ethyl acetate;

DOI:10.1021/jm960207w

Reference yield:

4-t-Butoxy-2,3,6-trifluoropyridine (169749-82-0) → (4-Chloro-5-fluoro-3-methoxy-pyridin-2-yl)-cyclopropyl-acetaldehyde (1025973-54-9)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) LDA, 2.) (MeO)3B, 3.) aq. 30percent H₂O₂

2: 91 percent / DEAD, Ph₃P / tetrahydrofuran / 0.17 h / Ambient temperature

3: 1.) N₂H₄*H₂O, 2.) O₂, 20percent aq. NaOH / 1.) n-PrOH, reflux, 3 h, 2.) MeOH, 3 d

4: 1.) LDA / 1.) THF, -78 deg C, 15 min, 2.) THF, a) -78 deg C, 1 h, b) 0 deg C, 1 h

5: CF₃COOH / 1 h / Ambient temperature

6: POCl₃, DMF / CH₂Cl₂

7: aq. HCl / 3 h / 80 - 85 °C

8: LiAlH₄ / tetrahydrofuran / 1 h / Ambient temperature

9: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) CH₂Cl₂, from -78 deg C to -10 deg C, 15 min

With hydrogenchloride; sodium hydroxide; lithium aluminium tetrahydride; oxalyl dichloride; Trimethyl borate; dihydrogen peroxide; oxygen; hydrazine hydrate; dimethyl sulfoxide; triethylamine; N,N-dimethyl-formamide; triphenylphosphine; trifluoroacetic acid; lithium diisopropyl amide; diethylazodicarboxylate; trichlorophosphate; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jm960207w

upstream raw materials:

2-(4-Chloro-5-fluoro-3-methoxy-pyridin-2-yl)-2-cyclopropyl-ethanol

3-chloro-2,4,5,6-tetrafluoropyridine

4-t-Butoxy-2,3,6-trifluoropyridine

4-tert-butoxy-2,5-difluoro-3-methoxypyridine

Refernces