1,4-Dibromobutane → Ethyl 1-(4-nitro-3-(2,2,2-trifluoroethoxy)phenyl)cyclopentane carboxylate
Reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:6][C:5]=1[O:16][CH2:17][C:18]([F:21])([F:20])[F:19])([O-:3])=[O:2].[H-].[Na+].Br[CH2:25][CH2:26][CH2:27][CH2:28]Br.[NH4+].[Cl-]>CN(C=O)C>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:28][CH2:27][CH2:26][CH2:25]2)=[CH:6][C:5]=1[O:16][CH2:17][C:18]([F:19])([F:20])[F:21])([O-:3])=[O:2]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
Ethyl 2-(4-nitro-3-(2,2,2-trifluoroethoxy)phenyl)acetate (0.5 g, mmol) was dissolved in 10 mL anhydrous DMF and NaH (60% wt. in oil, 0.13 g, mmol) was added at 0° C. The reaction mixture was stirred for 0.5 h at 25° C. and 1,4-dibromobutane (0.24 g, mmol) was added drop wise at 0° C. The reaction mixture was stirred at 0° C. for 1 h and saturated NH4Cl solution (10 mL) was added. The reaction mixture was extracted with EtOAc (3×20 mL) and the combined organic phases were washed with water (3×20 mL) and brine (20 mL), dried over MgSO4, filtered and concentrated under reduced pressure to give ethyl 1-(4-nitro-3-(2,2,2-trifluoroethoxy)phenyl)cyclopentane carboxylate (380 mg) as a colorless oil.
Workup
- stirringThe reaction mixture was stirred at 0° C. for 1 h
- extractionThe reaction mixture was extracted with EtOAc (3×20 mL)
- washthe combined organic phases were washed with water (3×20 mL) and brine (20 mL)
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-73e33f6abbc548f5bc93d4444c58268c
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08664249B2
Reaction notes
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