2,2,2-Trifluoroethylamine hydrochloride → 1-(2-Bromophenyl)-4,4,4-trifluorobutan-2-one
Reaction equation
Cl.[F:2][C:3]([F:7])([F:6])[CH2:4]N.N([O-])=O.[Na+].[Br:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH2:19][CH:20]=[O:21]>C(Cl)Cl.O.[Cl-].[Cl-].[Cl-].[Cl-].[Zr+4]>[Br:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH2:19][C:20](=[O:21])[CH2:4][C:3]([F:7])([F:6])[F:2]Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 78 °C
Procedure
To a solution of 2,2,2-trifluoroethanamine hydrochloride (27.1 g, 200 mmol) in DCM (400 ml) and water (50 ml) was added NaNO2 (15.43 g, 241 mmol) at 0° C. and stirred for 1 h. Then cooled to 78° C. then added 2-(2-bromophenyl)acetaldehyde (20 g, 100 mmol) and ZrCl4 (30.4 g, 130 mmol) and stirred for 2 h. The reaction mixture was quenched with MeOH (30 ml). The title compound was purified by separation methods A and E. (Yield 13.0 g).
Workup
- customThe reaction mixture was quenched with MeOH (30 ml)
- customThe title compound was purified by separation methods A and E
Sources & evidence
- ORD record
- ord-7795026eb1df4386921892ebba64e2c3
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09249127B2
Reaction notes
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