HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2065736Generated: October 31, 2026
Potassium Carbonate → Benzoic acid, 5-amino-2-chloro-4-methyl-, methyl ester
https://huagongshe.com/reaction/2065736
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Trimethylboroxine | HCID 574072 | — |
| Reactant | HCID 68606931 | HCID 68606931 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | Benzoic acid, 5-amino-2-chloro-4-methyl-, methyl ester | HCID 57423009 | 71.6% |
Reaction Steps
To a solution of 5-amino-6-bromo-2-chloro-benzoic acid methyl ester (0.5 g, 1.89 mmol) in dioxane (10 ml) and water (1 ml) was added potassium carbonate (0.784 g, 5.67 mmol), PdCl2(dppf) (0.54 g, 0.189 mmol) and trimethyl boroxine (0.276 ml, 1.985 mmol). The mixture was stirred at 110° C. for 18 hours, then cooled to room temperature and filtered. The filtrate was concentrated to dryness under reduced pressure. Purification of the residue by flash chromatography (hexanes:EtOAc 8:2) gave 0.270 g (71%) of 5-amino-2-chloro-4-methyl-benzoic acid methyl ester as a tan solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08288552B2 |
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| Source dataset | uspto-grants-2012_10 |
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| ORD ID | ord-d6d07fa856a2452187d218b821a7811b |
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| Source note | uspto-grants-2012_10 |
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