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ChemicalBook CAS DataBase List FLUCYTHRINATE
70124-77-5

FLUCYTHRINATE synthesis

2synthesis methods
Flucythrinate is commercially produced through esterification of two key intermediates: (+)-alpha-cyano-m-phenoxybenzyl alcohol and (+)-alpha-isopropyl-4-difluoromethoxyphenylacetyl chloride. The process begins with the synthesis of the acid chloride from the corresponding carboxylic acid using reagents like thionyl chloride in an organic solvent such as dichloromethane. This acid chloride is then reacted with the cyano-phenoxybenzyl alcohol in the presence of a base like pyridine to form the ester linkage, yielding flucythrinate. The reaction is conducted under controlled temperature and anhydrous conditions to ensure high yield and purity.
-

Yield:-

Reaction Conditions:

in dichloromethane

Steps:

11 Preparation of (+)-α-Cyano-m-phenoxybenzyl (+)-α-Isopropyl-4-difluoromethoxyphenylacetate
EXAMPLE 11 Preparation of (+)-α-Cyano-m-phenoxybenzyl (+)-α-Isopropyl-4-difluoromethoxyphenylacetate The compound (+)-α-cyano-m-phenoxybenzyl (+)-α-isopropyl-4-difluoromethoxyphenylacetate can be prepared by treating a solution of (+)-2-(4-difluoromethoxyphenyl)-3-methylbutyryl chloride in methylene chloride with α-cyano-m-phenoxybenzyl alcohol in methylene chloride and pyridine as described in Example 8 above. The compound (+)-α-cyano-m-phenoxybenzyl (+)-α-isopropyl-4-difluoromethoxyphenylacetate is a colorless viscous oil. ND23 =1.5432; NMR (CDCl3) δ6.8 to 7.5 (m, 13H, ArH); δ6.73 (t, J=74 Hz, 1H, OCHF2); δ6.30 and 6.23 (2S, 1H, CH--CN); δ3.27 [d, J=10 Hz, 1H, CH--CH(CH3)2 ].

References:

American Cyanamid Company US4377531, 1983, A

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