(Diethylamino)sulfur trifluoride → 1-fluoro-3-(2,4,6-trichloro-phenyl)-propan-2-one O-methyl-oxime
Reaction equation
[CH3:1][O:2][N:3]=[C:4]([CH2:7][C:8]1[C:13]([Cl:14])=[CH:12][C:11]([Cl:15])=[CH:10][C:9]=1[Cl:16])[CH2:5]O.C(N(S(F)(F)[F:23])CC)C>ClCCl>[CH3:1][O:2][N:3]=[C:4]([CH2:7][C:8]1[C:13]([Cl:14])=[CH:12][C:11]([Cl:15])=[CH:10][C:9]=1[Cl:16])[CH2:5][F:23]Participants
Conditions
- Temperature
- 20 °C
Procedure
To a stirred brown suspension of 1-hydroxy-3-(2,4,6-trichloro-phenyl)-propan-2-one O-methyl-oxime (33 g; 117 mmol) in dichloromethane (235 ml) at −20° C. under nitrogen was added dropwise a solution of diethylaminosulfur trifluoride (16 ml; 123 mmol) in dichloromethane (62 ml). During addition, temperature rose to −10° C. The mixture turned to a brown orange solution which was allowed to warm at 20° C. and was stirred for 2 hours. The organic solution was washed with saturated hydrogen carbonate solution (200 ml), 1N hydrochloric acid (200 ml), brine (200 ml) and dried over sodium sulfate. The solvent was removed in vacuo to afford 37 g (110% of theory) of crude 1-fluoro-3-(2,4,6-trichloro-phenyl)-propan-2-one O-methyl-oxime (isomers E/Z) as a brown oil.
Workup
- additionDuring addition, temperature
- customrose to −10° C
- washThe organic solution was washed with saturated hydrogen carbonate solution (200 ml), 1N hydrochloric acid (200 ml), brine (200 ml)
- dry with materialdried over sodium sulfate
- customThe solvent was removed in vacuo
Sources & evidence
- ORD record
- ord-225899cc8f5143a88ceb5d113038e135
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08552049B2
Reaction notes
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