1-Fluoro-3-adamantanecarboxylic acid synthesis

9synthesis methods

Product Name:1-Fluoro-3-adamantanecarboxylic acid
CAS Number:880-50-2
Molecular formula:C11H15FO2
Molecular Weight:198.23

Tricyclo[3.3.1.13,7]decane-1-carbonyl fluoride, 3-fluoro- (9CI)

96962-78-6
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880-50-2
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Yield:880-50-2 83%

Reaction Conditions:

with lithium hydroxide monohydrate;sodium hydroxide at 60; for 8 h;

Steps:

3-Fluoroadamantane-1-carboxylic acid (1)

A solution of 3-hydroxyadamantane-1-carboxylic acid (5) (10 g, 0.051 mmol) in dichloromethane (200 mL) was added dropwise to a solution of Ishikawa's reagent (20.1 g, 0.095 mol) in dichloromethane (100 mL) with stirring at 0-5 over 1 h. The mixture was stirred for another 2 h at the same temperature and concentrated in vacuo. The resulting fluoroanhydride 6 was suspended in 1 M aqueous solution of NaOH (100 mL)and heated at 60 °C for 8 h. Then, the solution was washed with dichloromethane (100 mL) and acidified with HCl to weakly acidic pH. The resulting precipitate was collected byfiltration, washed with water (200 mL), and dried to obtain acid 1 (8.7 g, 83%), a white crystalline compound, m.p.151 °C . MS (EI, 70 eV), m/z (Irel (%)): 198 []+ (6), 179[M - F]+ (3), 153 [AdF]+ (100), 133 [Ad]+ (31). Found (%):, 66.69; , 7.64. C11H15F2. Calculated (%): , 66.65;, 7.63.

References:

Gladkikh;Danilov;D’yachenko;Burmistrov;Butov;Novakov [Russian Chemical Bulletin,2022,vol. 71,# 9,p. 1998 - 2005][Izv. Akad. Nauk, Ser. Khim.,2022,# 9,p. 1998 - 2005]

Tricyclo[3.3.1.13,7]decane-1-carboxylic acid, 3-fluoro-, methyl ester

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880-50-2
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References

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References