Hydrochloric Acid → 3-Chloro-2,4,5-trifluorobenzoic Acid
Reaction equation
N(OC(C)(C)C)=O.N[C:9]1[C:10]([F:20])=[C:11]([CH:15]=[C:16]([F:19])[C:17]=1[F:18])[C:12]([OH:14])=[O:13].[ClH:21]>C(#N)C>[Cl:21][C:9]1[C:10]([F:20])=[C:11]([CH:15]=[C:16]([F:19])[C:17]=1[F:18])[C:12]([OH:14])=[O:13]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
9.3 g of anhydrous cuprous chloride and 8.8 g of tert-butyl nitrite were added to 150 ml of acetonitrile and under stirring and heating at 60° C., 11 g of 3-amino-2,4,5-trifluorobenzoic acid 26 (a commercial product) was added. The mixture was stirred for 20 minutes. After cooling, 500 ml of 15% hydrochloric acid was added and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate and the solvent was then removed under reduced pressure. Finally the residue was subjected to silica gel (100 g) column chromatography using chloroform as an eluent. The procedure gave 8.4 g of 3-chloro-2,4,5-trifluorobenzoic acid 27 as colorless needles.
Workup
- stirringThe mixture was stirred for 20 minutes
- temperatureAfter cooling
- extractionthe mixture was extracted with ethyl acetate
- dry with materialThe extract was dried over anhydrous sodium sulfate
- customthe solvent was then removed under reduced pressure
Sources & evidence
- ORD record
- ord-89dcc0c1c1fb42d3885c0cd07642c891
- Source dataset
- uspto-grants-1994_02
- Patent number
- US05286723
Reaction notes
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