HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 60907Generated: October 26, 2026
Cesium fluoride → Methyl 5-methyl-2-(pyridin-2-yl)benzoate
https://huagongshe.com/reaction/60907
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium fluoride | HCID 25953 | — |
| Reactant | 2-(Tributylstannyl)pyridine | HCID 607784 | — |
| Reactant | Methyl 2-bromo-5-methylbenzoate | HCID 15110996 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | Methyl 5-methyl-2-(pyridin-2-yl)benzoate | HCID 67982793 | — |
Reaction Steps
A mixture of methyl 2-bromo-5-methylbenzoate (0.629 g, 2.747 mmol), 2-(tributylstannyl)pyridine (1.32 g, 3.585 mmol), CsF (0.834 g, 5.494 mmol), Pd(PPh3)4 (0.4 g, 0.27 mmol), and CuI (0.105 g, 0.549 mmol) in DMF (20 mL) was degassed for 10 min and then heated in the microwave reactor for 30 min at 130° C. The mixture was cooled and the solvent was removed in vacuo. The crude was dissolved with EtOAc and then washed with saturated NaHCO3 and dried over Na2SO4. The solvent was removed in vacuo to obtain the crude, which was purified by silica gel to obtain the title compound. ESI-MS (m/z): 228 [M+1]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09440982B2 |
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| Source dataset | uspto-grants-2016_09 |
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| ORD ID | ord-f5515e795507478b88057ba06393f836 |
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| Source note | uspto-grants-2016_09 |
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