1-Bromo-2-methylpropane → Ethyl 4-methyl-2-(4-nitro-3-(2,2,2-trifluoroethoxy)phenyl)pentanoate
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+].[CH2:24](Br)[CH:25]([CH3:27])[CH3:26].[NH4+].[Cl-]>CN(C=O)C>[CH3:24][CH:25]([CH3:27])[CH2:26][CH:10]([C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[C:5]([O:16][CH2:17][C:18]([F:19])([F:20])[F:21])[CH:6]=1)[C:11]([O:13][CH2:14][CH3:15])=[O:12]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 (4 g, 16.2 mmol) was dissolved in 50 mL anhydrous DMF and NaH (60% wt. in oil, 0.846 g, 21.1 mmol) was added at 0° C. The reaction mixture was stirred for 0.5 h at 25° C. and isobutyl bromide (2.12 mL, 19.5 mmol) was added drop wise at 0° C. The reaction mixture was stirred at 0° C. for 1 h and saturated NH4Cl solution 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 4-methyl-2-(4-nitro-3-(2,2,2-trifluoroethoxy)phenyl)pentanoate (1.5 g) 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-4a546744bd0d47e896f132922a928cc1
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08664249B2
Reaction notes
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