Carbon Dioxide → 2,3,5,6-Tetrafluorobenzoic Acid
Reaction equation
C([Li])CCC.[F:6][C:7]1[C:12]([F:13])=[CH:11][C:10]([F:14])=[C:9]([F:15])[CH:8]=1.[C:16](=[O:18])=[O:17].Cl>O1CCCC1.O>[F:6][C:7]1[C:12]([F:13])=[CH:11][C:10]([F:14])=[C:9]([F:15])[C:8]=1[C:16]([OH:18])=[O:17]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -70 °C
Procedure
n-Butyllithium (2.7M solution in n-hexane, 148 cm3) was added dropwise over a period of one hour to a stirred solution of 2,3,5,6-tetrafluorobenzene (60 g) in dry tetrahydrofuran (200 cm3) maintained at -70° C. under a nitrogen atmosphere, after which the mixture was stirred at -70° C. for a further one hour. Carbon dioxide gas was passed into the mixture over a period of 4 hours during which time the temperature was allowed to warm up to the ambient value (ca. 22° C.). After adding water and acidifying with dilute hydrochloric acid, the mixture was extracted with diethyl ether and the extracts dried over anhydrous magnesium sulphate. The product was obtained by removal of the solvent by evaporation under reduced pressure to give 2,3,5,6-tetrafluorobenzoic acid (42.5 g), mp. 152°-154° C.
Workup
- temperatureto warm up to the ambient value (ca. 22° C.)
- extractionthe mixture was extracted with diethyl ether
- dry with materialthe extracts dried over anhydrous magnesium sulphate
- customThe product was obtained by removal of the solvent by evaporation under reduced pressure
Sources & evidence
- ORD record
- ord-cffdf863ac3c4e108b0eef30a28b5def
- Source dataset
- uspto-grants-1989_08
- Patent number
- US04853414
Reaction notes
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