Dimethyl Sulfoxide → HCID 14855594, compound
Reaction equation
C(O[O:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][C:8]=1[F:14])(=O)CC.[C:15](=[O:18])([O-])[O-:16].[K+].[K+].[CH3:21]S(C)=O.[F:25][C:26]1[CH:27]=[C:28]([N+:33]([O-:35])=[O:34])[CH:29]=[CH:30][C:31]=1F.[CH2:36](OCC)[CH3:37]>>[F:14][C:8]1[CH:9]=[C:10]([O:13][C:31]2[CH:30]=[CH:29][C:28]([N+:33]([O-:35])=[O:34])=[CH:27][C:26]=2[F:25])[CH:11]=[CH:12][C:7]=1[O:6][CH:36]([CH3:37])[C:15]([O:16][CH3:21])=[O:18]Participants
Conditions
- Temperature
- 50 °C
Procedure
To a stirred mixture of methyl 2-(2-fluoro-4-hydroxyphenoxy propanoate (4.0 g, 0.019 mole), potassium carbonate (2.9 g, 0.021 mole) and dimethyl sulfoxide (25 ml), was added 3,4-difluoronitrobenzene (3.0 g, 0.019 mole), all at once. The temperature was raised to 50° C., and held there for 19 hours. After this time, the resultant mixture was cooled to room temperature, then diethyl ether (50 ml) was added. This was filtered, and the filtrate was diluted with additional diethyl ether (150 ml). The latter solution was washed with 2N HCL (2×100 ml), then water (3×100 ml). After drying (MgSO4) and filtering, the diethyl ether was removed by distillation. A brown viscous oil resulted (6.2 grams, 92 percent). NMR spectroscopy (1H, 19F) confirmed the structure as consistent with the structure for the desired product. It was used directly in the next step without further purification.
Workup
- filtrationThis was filtered
- additionthe filtrate was diluted with additional diethyl ether (150 ml)
- washThe latter solution was washed with 2N HCL (2×100 ml)
- dry with materialAfter drying (MgSO4)
- filtrationfiltering
- customthe diethyl ether was removed by distillation
- customA brown viscous oil resulted (6.2 grams, 92 percent)
Sources & evidence
- ORD record
- ord-9610b0a11ac341c392ae97bf7f41caa2
- Source dataset
- uspto-grants-1989_12
- Patent number
- US04888050
Reaction notes
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