Diethyl Ether → 1-[3-Ethoxy-4-(trifluoromethyl)phenyl]ethanone
Reaction equation
C(O[C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[C:12]([F:15])([F:14])[F:13])C#N)C.C([Si](C)(C)Cl)(C)(C)C.C[Mg]Br.C([O:29]CC)C.[NH4+].[Cl-].[CH2:34]1[CH2:38][O:37][CH2:36][CH2:35]1>[Cu]Br>[CH2:38]([O:37][C:36]1[CH:35]=[C:6]([C:9](=[O:29])[CH3:10])[CH:5]=[CH:4][C:11]=1[C:12]([F:15])([F:14])[F:13])[CH3:34]Participants
Reactant 6
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -70 °C
Procedure
To a solution of 3-ethoxy-4-trifluoromethyl-benzonitrile from step 5 (5.00 g, 23.2 mmol), copper(I) bromide (100 mg, 0.7 mmol), tert.-butyldimethylchlorosilane (4.20 g, 27.9 mmol) in dry THF (30 mL) at −70° C. was drop wise added a 3 M methylmagnesium bromide solution in diethyl ether (13.2 mL, 39.6 mmol). The mixture was stirred at −70° C. for 10 min, then was warmed up to 0° C. and stirring was continued at 0° C. for further 2 h under nitrogen atmosphere. Poured the reaction mixture onto ice and sat. NH4Cl-sol., extracted three times with diethyl ether, washed the combined organic layers with brine, dried over MgSO4. Removal of the solvent in vacuum left a brown oil, which was purified by silica gel column chromatography with heptane/EtOAc 4:1 to give the title compound as a yellow liquid (1.84 g, 34%). MS (EI) 232 [M].
Workup
- customat −70° C.
- temperaturewas warmed up to 0° C.
- stirringstirring
- waitwas continued at 0° C. for further 2 h under nitrogen atmosphere
- extraction, extracted three times with diethyl ether
- washwashed the combined organic layers with brine
- dry with materialdried over MgSO4
- customRemoval of the solvent in vacuum
- waitleft a brown oil, which
- customwas purified by silica gel column chromatography with heptane/EtOAc 4:1
Sources & evidence
- ORD record
- ord-8edfbd7ffe9544b4b36944cfa7743048
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08093263B2
Reaction notes
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