Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 4-Bromophenol | HCID 7808 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 4-Chloro-2-methylpyridine | HCID 581392 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | HCID 59287317 | HCID 59287317 | — |
Reaction Steps
4-Bromophenol (1.0 g, 5.78 mmol) was added to a solution of sodium hydride (0.3 g, 7.51 mmol) in N-methylpyrrolidone (10 ml). After stiffing for 10 minutes, 4-chloro-2-methylpyridine (0.96 g, 7.51 mmol) was added. The reaction mixture was heated at 250° C. for 45 minutes under microwave irradiation. After cooling to room temperature the mixture was diluted with diethyl ether and washed with water. The solution was then extracted with additional diethyl ether, the organic layer dried (Na2SO4) and the solvent evaporated in vacuo. The crude product was purified by column chromatography (silica gel; DCM as eluent). The desired fractions were collected and evaporated in vacuo to yield intermediate D10 (1.34 g, 88%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08748621B2 |
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| Source dataset | uspto-grants-2014_06 |
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| ORD ID | ord-a2589e714a494f6cbf381c4ef76e07aa |
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| Source note | uspto-grants-2014_06 |
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