Water → Methyl-6-chloro-3-(chloro(hydroxyimino)methyl)-2-fluorobenzoate
Reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[C:9]([Cl:10])=[CH:8][CH:7]=[C:6]([CH:11]=[N:12][OH:13])[C:5]=1[F:14].C1C(=O)N([Cl:23])C(=O)C1.O.CCOC(C)=O>CN(C=O)C>[CH3:1][O:2][C:3](=[O:15])[C:4]1[C:9]([Cl:10])=[CH:8][CH:7]=[C:6]([C:11]([Cl:23])=[N:12][OH:13])[C:5]=1[F:14]Participants
6
Conditions
- Temperature
- 50 °C
Procedure
To a solution of methyl-6-chloro-2-fluoro-3-((hydroxyimino)methyl)benzoate (553 mg, 2388 μmol) in DMF (5.3 ml) at 0° C. was added NCS (351 mg, 2626 μmol). The mixture was heated to 50° C. for 10 min after which time LCMS analysis indicated the reaction was complete. The mixture was cooled to RT, water was added followed by EtOAc, the layers were separated, and the aqueous was extracted with EtOAc (3×). The combined organic layers were washed with brine (2×), dried over MgSO4, filtered and concentrated to afford the title compound as a yellow viscous oil, which solidified upon evacuation under reduced pressure.
Workup
- temperatureThe mixture was cooled to RT
- customthe layers were separated
- extractionthe aqueous was extracted with EtOAc (3×)
- washThe combined organic layers were washed with brine (2×)
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-de174a9722b44a5593810b722457d950
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08163742B2
Reaction notes
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