Triethylamine → 5-Bromo-2-(trifluoromethoxy)benzonitrile
Reaction equation
C([N:3]([CH2:6][CH3:7])CC)C.CCCP(=O)=O.[Br:14][C:15]1[CH:16]=C[C:18]([O:23][C:24]([F:27])([F:26])[F:25])=[C:19]([CH:22]=1)C=O.Cl.ON.C(=O)(O)[O-].[Na+]>CN(C=O)C>[Br:14][C:15]1[CH:22]=[CH:19][C:18]([O:23][C:24]([F:25])([F:26])[F:27])=[C:7]([CH:16]=1)[C:6]#[N:3]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
Triethylamine (1.14 mL, 8.18 mmol) and propylphosphonic anhydride (cyclic trimer) (ca. 1.7 M solution in ethyl acetate, 4.8 mL, 8.18 mmol) were added in this order to a solution of 5-bromo-2-(trifluoromethoxy)benzaldehyde (2.00 g, 7.43 mmol) and hydroxyamine hydrochloride (568 mg, 8.18 mmol) in DMF (7.5 mL), and the mixture was stirred at 100° C. for 8 hours. The reaction solution was poured to a saturated sodium bicarbonate aqueous solution, followed by extraction with ethyl acetate. The obtained organic layer was washed with brine and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography [elute: hexane/ethyl acetate=100/0-98/2] to obtain the title compound (1.71 g, yield: 86%).
Workup
- extractionfollowed by extraction with ethyl acetate
- washThe obtained organic layer was washed with brine
- dry with materialdried over anhydrous sodium sulfate
- distillationthe solvent was distilled off under reduced pressure
- customThe obtained residue was purified by silica gel column chromatography [elute: hexane/ethyl acetate=100/0-98/2]
Sources & evidence
- ORD record
- ord-fbffe86c42274eaba2b208d8911af331
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09150575B2
Reaction notes
Loading…