1,1,1-Trifluoro-2-iodoethane → 4-Iodo-1-(2,2,2-trifluoroethyl)-1H-pyrazole
Reaction equation
[I:1][C:2]1[CH:3]=[N:4][NH:5][CH:6]=1.[F:7][C:8]([F:12])([F:11])[CH2:9]I>CN(C=O)C>[I:1][C:2]1[CH:3]=[N:4][N:5]([CH2:9][C:8]([F:12])([F:11])[F:7])[CH:6]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
A mixture of 4-iodo-1H-pyrazole (960 mg, 5 mmol), 2,2,2-trifluoroethyl iodide (3.13 g, 15 mmol) and CS2CO3 (2.4 g, 7.7 mmol) in DMF (5 ml) is heated at 60° C. with stirring overnight. After cooling, the reaction mixture is partitioned between water (50 ml) and ether (20 ml). The organic layer is separated, dried (MgSO4) and concentrated to afford the title compound as an oil which solidified upon standing 1.0 g (72%). 1HNMR (CDCl3): δ (ppm) 4.70 (m, 2H), 7.56 (s, 1H), 7.59 (s, 1H).
Workup
- temperatureAfter cooling
- customthe reaction mixture is partitioned between water (50 ml) and ether (20 ml)
- customThe organic layer is separated
- dry with materialdried (MgSO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-12ed34ecab0740fe9a80eddc787edeb3
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07705030B2
Reaction notes
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