Reaction equation
S(=O)(=O)(O)O.Cl[C:7]#[C:8][C:9]1[CH:14]=[C:13]([F:15])[C:12]([F:16])=[CH:11][C:10]=1[F:17].CC([O:22]C)(C)C.[OH2:24]>>[F:17][C:10]1[CH:11]=[C:12]([F:16])[C:13]([F:15])=[CH:14][C:9]=1[CH2:8][C:7]([OH:22])=[O:24]Participants
5
Conditions
- Temperature
- 100 °C
Procedure
50 ml of concentrated sulphuric acid was added to 1-chloroethynyl-2,4,5-trifluorobenzene of formula IV, X═Cl and the mixture heated to 100° C. and left to stir for 1 hour. 50 ml of MTBE and 100 ml of water were then added. The phases were separated and the aqueous phase was re-extracted with 2×50 ml of MTBE. The combined organic phases were counter extracted with 3×50 ml of aqueous NaHCO3 and put to one side. The three aqueous phases of NaHCO3 were recombined and the resulting phase was acidified with hydrochloric acid and then extracted with 3×50 ml of MTBE. The organic phases were concentrated to a residue obtaining 0.25 g of 2,4,5-trifluorophenylacetic acid of formula (I) with a molar yield of 25%.
Workup
- waitleft
- customThe phases were separated
- extractionthe aqueous phase was re-extracted with 2×50 ml of MTBE
- extractionThe combined organic phases were counter extracted with 3×50 ml of aqueous NaHCO3
- extractionextracted with 3×50 ml of MTBE
- concentrationThe organic phases were concentrated to a residue
Sources & evidence
- ORD record
- ord-266f8b4c0c3344e69418dd7c1bdcc3b4
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08835679B2
Linked notes
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