Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 2,3-Difluoro-4-iodobenzonitrile | HCID 68809189 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 68809527 | HCID 68809527 | 94.7% |
Reaction Steps
Sodium hydride (60 mg, 2.5 mmol) was slurried in DMF (15 mL) and treated with dry methanol (120 μl, 96 mg, 3.0 mmol). After stirring for 10 minutes at 25° C., the solution was cooled to −25° C. and treated with 2,3-difluoro-4-iodobenzonitrile (500 mg, 1.9 mmol). After 25 minutes, the mixture was quenched by addition of 10% citric acid solution (5 mL) and warmed to 25° C. The mixture was extracted with ethyl ether (2×15 mL), the combined ether phases washed with water (5 mL), brine, dried (sodium sulfate) and evaporated to give 3-fluoro-4-iodo-2-methoxybenzonitrile (500 mg, 1.8 mmol): LC/MS (m/z=277).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07314849B2 |
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| Source dataset | uspto-grants-2008_01 |
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| ORD ID | ord-2a9398f053734df2b3b8e1a6a9968d7b |
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| Source note | uspto-grants-2008_01 |
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