HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2039156Generated: November 3, 2026
Azobisisobutyronitrile → Methyl 3-(bromomethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate
https://huagongshe.com/reaction/2039156
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Azobisisobutyronitrile | HCID 6547 | — |
| Reactant | N-bromobutanimide | HCID 67184 | — |
| Reactant | 2-Methyl-4-methoxycarbonylphenylboronic acid, pinacol ester | HCID 11087024 | — |
| Solvent | Carbon Tetrachloride | HCID 5943 | — |
| Product | Methyl 3-(bromomethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate | HCID 59610334 | 103% |
Reaction Steps
The solution of 3-Methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester (3.71 g, 13.4 mmol), NBS (2.39 g, 13.4 mmol), and AIBN (235 mg) in CCl4 (20 ml) was heated at 80° C. for 14 hours. The mixture was cooled to 25° C., and was filtered and washed with CCl4. The solution was concentrated under reduced pressure, and was diluted with EtOAc. The solution was washed with water and brine and was dried with Na2SO4. Concentration gave 3-Bromomethyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester (4.9 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08575118B2 |
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| Source dataset | uspto-grants-2013_11 |
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| ORD ID | ord-34577f3f1727454d95d8a6ff90e8553f |
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| Source note | uspto-grants-2013_11 |
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