HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2070299Generated: October 26, 2026
Sodium Carbonate → 3-Chloro-4-(2-methyl-5-nitrophenyl)pyridine
https://huagongshe.com/reaction/2070299
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 2-Bromo-4-nitrotoluene | HCID 82189 | — |
| Reactant | 3-Chloro-4-pyridineboronic acid hydrate | HCID 17998756 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | 3-Chloro-4-(2-methyl-5-nitrophenyl)pyridine | HCID 22040820 | — |
Reaction Steps
Nitrogen was bubbled through a solution of 2-bromo-1-methyl-4-nitrobenzene (1 eq) in dimethoxyethane and water (3:1) for 0.5 h. Bis(diphenylphosphino)ferrocene Palladium(II)chloride (0.05 eq) followed by 3-chloro-4-pyridine boronic acid hydrate (1 eq) and sodium carbonate (3 eq) was added and the mixture was heated to 90° C. for 16 h under nitrogen. The reaction mixture was concentrated and partitioned between ethyl acetate and water. The organic layer was washed with brine and dried with sodium sulfate and concentrated. Purification on silica gel gave 3-chloro-4-(2-methyl-5-nitrophenyl)pyridine. MS: MH+=248.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08299108B2 |
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| Source dataset | uspto-grants-2012_10 |
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| ORD ID | ord-36e5c652bc4540d59ff028cf27501d51 |
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| Source note | uspto-grants-2012_10 |
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