1- and 2-fluoroalkyl carboxylates

The 2-fluoroalkyl esters, e.g. FCH2CH2CO2Me are readily accessible by the base-catalyzed acylation of fluorohydrines. A two-step procedure is required to prep. the 1-fluoroalkyl esters: conversion of alk-1-enyl carboxylates (\"ene esters\") into the 2-bromo-1-fluoroalkyl esters by simultaneous treatment with N-bromosuccinimide and HF followed by the reductive replacement of bromine by tributyltin hydride. Alka-1,3-dienyl carboxylates (\"diene esters\") undergo 1,4-addn. of bromine and fluorine. The resulting 4-bromo-1-fluoralk-2-enyl carboxylates undergo a substitution reaction with sodium benzenesulfinate to afford the sulfones or oxidn. with DMSO to yield the 4-oxo derivs. 2-Fluoroethanol was added to NaH followed by AcOH to give 2-fluoroacetate. 2-Bromo-1-fluoroethyl acetate (prepn. given) and Bu3SnH were kept at 90 Deg for 1 h to give 1-fluoroethyl acetate. [on SciFinder (R)]

Published in:
Liebigs Annalen, 5, 849-53
CAN 123:111530 23-17 Aliphatic Compounds Inst. Chim. org.,Univ. Lausanne,Lausanne-Dorigny,Switz. Journal 0947-3440 written in English. 108-05-4 (Vinyl acetate); 371-62-0 (2-Fluoroethanol); 693-38-9 (Vinyl palmitate); 1813-13-4; 3109-99-7; 17574-85-5; 17574-86-6; 35694-19-0; 35694-20-3; 52062-24-5; 52062-25-6; 74322-79-5; 110500-35-1; 150020-39-6; 165614-45-9; 165614-46-0; 165614-47-1; 165614-48-2; 165614-49-3; 165614-50-6; 165614-51-7; 165614-52-8; 165614-53-9; 165614-54-0 Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of fluoroalkyl carboxylates); 165614-20-0P; 165614-21-1P; 165614-22-2P; 165614-23-3P; 165614-24-4P; 165614-25-5P; 165614-26-6P; 165614-27-7P; 165614-28-8P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of fluoroalkyl carboxylates); 462-26-0P; 1786-46-5P; 137555-31-8P; 165614-09-5P; 165614-10-8P; 165614-11-9P; 165614-12-0P; 165614-13-1P; 165614-14-2P; 165614-15-3P; 165614-16-4P; 165614-17-5P; 165614-18-6P; 165614-19-7P; 165614-29-9P; 165614-30-2P; 165614-31-3P; 165614-32-4P; 165614-33-5P; 165614-34-6P; 165614-35-7P; 165614-36-8P; 165614-37-9P; 165614-38-0P; 165614-39-1P; 165614-40-4P; 165614-41-5P; 165614-42-6P; 165614-43-7P; 165614-44-8P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of fluoroalkyl carboxylates)

 Record created 2006-03-03, last modified 2018-01-27

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