N-Methoxy-N-methyl-3-(1,1,2,2-tetrafluoroethoxy)benzamide → 1-[3-(1,1,2,2-Tetrafluoroethoxy)phenyl]ethanone
Reaction equation
CON(C)[C:4](=[O:18])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]([F:17])([F:16])[CH:13]([F:15])[F:14])[CH:6]=1.[CH3:20][Mg]Br>C1COCC1>[F:17][C:12]([F:16])([O:11][C:7]1[CH:6]=[C:5]([C:4](=[O:18])[CH3:20])[CH:10]=[CH:9][CH:8]=1)[CH:13]([F:14])[F:15]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
N-methoxy-N-methyl-3-(1,1,2,2-tetrafluoroethoxy)benzamide (7.5 g, 25.2 mmol) was dissolved in THF (84 mL) and cooled to −78° C. Methyl magnesium bromide (3N in diethyl ether, 21.03 mL, 63.1 mmol) was added dropwise and the resulting reaction mixture was stirred for 30 min. The reaction was warmed to 25° C. over 30 minutes and then was quenched by addition to an Erlenmeyer flask containing ice and saturated ammonium chloride solution. This mixture was extracted with EtOAc, the organic layers were collected and dried with anhydrous magnesium sulfate, then filtered and concentrated. Crude material obtained corresponds to 1-[3-(1,1,2,2-tetrafluoroethoxy)phenyl]ethanone. 1H NMR (400 MHz, CDCl3) δ 2.62 (s, 3H), 5.96 (t, t, J=53, 2.7 Hz, 1H), 7.43 (d, J=8.1 Hz, 1H), 7.51 (t, J=8.0 Hz, 1H), 7.80 (s, 1H), 7.88 (d, J=7.8 Hz, 1H).
Workup
- customthe resulting reaction mixture
- temperatureThe reaction was warmed to 25° C. over 30 minutes
- customwas quenched by addition to an Erlenmeyer flask
- additioncontaining ice and saturated ammonium chloride solution
- extractionThis mixture was extracted with EtOAc
- customthe organic layers were collected
- dry with materialdried with anhydrous magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-075c418ed7ce4f118dd98dd015e5e640
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09126976B2
Reaction notes
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