HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1501232Generated: October 25, 2026
Sodium Carbonate → Tert-butyl 2-methyl-4-(1-phenylvinyl)benzoate
https://huagongshe.com/reaction/1501232
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | trans-2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)styrene | HCID 2774014 | — |
| Reactant | tert-Butyl 4-bromo-2-methylbenzoate | HCID 53432590 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | 1,4-Dioxane--water (1/1) | HCID 21886435 | — |
| Product | Tert-butyl 2-methyl-4-(1-phenylvinyl)benzoate | HCID 89580861 | 91% |
Reaction Steps
To a solution of tert-butyl 4-bromo-2-methylbenzoate (2 g, 7 mmol) in dioxane/water (50 mL, 4:1) was added styrylboronic acid pinacol ester (1.64 g, 7 mmol), tetrakis(triphenylphosphine)palladium (0.7 mmol, 0.904 g), sodium carbonate (21 mmol, 2.3 g). The mixture was stirred at 90° C. under nitrogen gas atmosphere for 18 hours. LC-MS showed the start material has been consumed. Then evaporated the solvent and purified by column chromatography (silica gel, petroleum ether/ethyl acetate=30:1) to give tert-butyl 2-methyl-4-(1-phenylvinyl)benzoate (1.8 g, 91%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09206128B2 |
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| Source dataset | uspto-grants-2015_12 |
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| ORD ID | ord-669c9f2a3d334c60b2ed7bc5ddbf48bb |
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| Source note | uspto-grants-2015_12 |
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