4-fluorobicyclo[2.2.2]octane-1-carboxylic acid

Base Information

• Chemical Name: 4-fluorobicyclo[2.2.2]octane-1-carboxylic acid
• CAS No.: 78385-84-9
• Molecular Formula: C9H13FO2
• Molecular Weight: 172.19700
• Mol file: 78385-84-9.mol

Synonyms:

Chemical Property of 4-fluorobicyclo[2.2.2]octane-1-carboxylic acid

Chemical Property:

• PSA: 37.30000
• LogP: 2.13350
• Storage Temp.: 2-8°C

Purity/Quality:

99.3% ^*data from raw suppliers

4-Fluorobicyclo[2.2.2]octane-1-carboxylicacid 97.0% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4-fluorobicyclo[2.2.2]octane-1-carboxylic acid

There total 14 articles about 4-fluorobicyclo[2.2.2]octane-1-carboxylic acid 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: 96.0%

methyl 4-fluorobicyclo<2.2.2>octane-1-carboxylate (78385-85-0) → 4-fluorobicyclo<2.2.2>octane-1-carboxylic acid (78385-84-9)

Guidance literature:

With potassium hydroxide; water; In ethanol; for 16h; Ambient temperature;

DOI:10.1021/jo00136a028

Reference yield:

ethyl 1-acetyl-4-oxocyclohexane-1-carboxylate (72653-21-5) → 4-fluorobicyclo<2.2.2>octane-1-carboxylic acid (78385-84-9)

Guidance literature:

Multi-step reaction with 8 steps

1: methanol

2: H₂O/KOH / ethanol / 16 h / Ambient temperature

3: hydrazine hydrate, KOH / bis-(2-hydroxy-ethyl) ether / 10 h / Heating

4: 91 percent / concn H₂SO₄ / 1,2-dichloro-ethane / 20 h / Heating

5: 92 percent / BF₃*OEt₂ / Ambient temperature

6: 94 percent / NaOMe / methanol / 2 h / Heating

7: 92 percent / SF₄ / 24 h / Ambient temperature

8: 96 percent / H₂O/KOH / ethanol / 16 h / Ambient temperature

With potassium hydroxide; sulfuric acid; sulfur tetrafluoride; boron trifluoride diethyl etherate; water; sodium methylate; hydrazine hydrate; In methanol; ethanol; 1,2-dichloro-ethane; diethylene glycol;

DOI:10.1021/jo00136a028

Reference yield:

1,5-di-tert-butyl 3-ethyl 3-acetylpentane-1,3,5-tricarboxylate (72653-14-6) → 4-fluorobicyclo<2.2.2>octane-1-carboxylic acid (78385-84-9)

Guidance literature:

Multi-step reaction with 10 steps

1: KOAc/Ac₂O / 2 h / Heating

2: 250 - 260 °C / 10 Torr

3: methanol

4: H₂O/KOH / ethanol / 16 h / Ambient temperature

5: hydrazine hydrate, KOH / bis-(2-hydroxy-ethyl) ether / 10 h / Heating

6: 91 percent / concn H₂SO₄ / 1,2-dichloro-ethane / 20 h / Heating

7: 92 percent / BF₃*OEt₂ / Ambient temperature

8: 94 percent / NaOMe / methanol / 2 h / Heating

9: 92 percent / SF₄ / 24 h / Ambient temperature

10: 96 percent / H₂O/KOH / ethanol / 16 h / Ambient temperature

With potassium hydroxide; sulfuric acid; sulfur tetrafluoride; boron trifluoride diethyl etherate; water; sodium methylate; potassium acetate; acetic anhydride; hydrazine hydrate; In methanol; ethanol; 1,2-dichloro-ethane; diethylene glycol;

DOI:10.1021/jo00136a028

upstream raw materials:

methyl 4-fluorobicyclo<2.2.2>octane-1-carboxylate

ethyl 1-acetyl-4-oxocyclohexane-1-carboxylate

1,5-di-tert-butyl 3-ethyl 3-acetylpentane-1,3,5-tricarboxylate

4-methoxybicyclo<2.2.2>octane-1-carboxylic acid

Downstream raw materials:

amino-4-fluorobicyclo[2.2.2]octane

1,4-Difluor-bicyclo<2.2.2>octan

4-Fluoro-bicyclo[2.2.2]octane-1-carbonyl chloride

4-fluoro-bicyclo(2.2.2)octane-1-carboxylic fluoride

Refernces

• 1、 Adcock, William,Abeywickrema, Anil N.. "Synthesis of 4-Substituted Bicyclooct-1-yl Fluorides". . p. 2951 - 2957. Retrieved 2007/10/02.