HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1490562Generated: October 31, 2026
3-Bromobenzonitrile → 3-bromo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile
https://huagongshe.com/reaction/1490562
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 3-Bromobenzonitrile | HCID 23381 | — |
| Reagent | Bis(pinacolato)diborane | HCID 2733548 | — |
| Reagent | 3-pyridin-2-yl-2-(3-pyridin-2-yl-1H-1,3,2-benzodiazaborol-2-yl)-1H-1,3,2-benzodiazaborole | HCID 122380799 | — |
| Catalyst | Bis(1,5-cyclooctadiene)dimethoxydiiridium | HCID 76001521 | — |
| Solvent | Cyclopentyl methyl ether | HCID 138539 | — |
| Product | 3-bromo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile | HCID 11404046 | 55% |
Reaction Steps
The general procedure A was followed using 3-bromobenzonitrile (91.0 mg, 0.5 mmol) and B2pin2 (126.9 mg, 0.75 mmol, 1.5 eq.) as starting material. The resulting mixture was allowed to stir 48 hours at 125 oC. 5r was obtained as white solid (85.2 mg, 55%) after purification by silica gel flash chromatography (EtOAc/PE=1:15 v/v). m.p.: 81-83 oC.
Provenance & Evidence
| DOI | 10.1021/jacs.5b05252 |
|---|
| Source dataset | Borylation dataset from Roche |
|---|
| ORD ID | ord-e6f10914d6d7482292ff5149d3753b3f |
|---|
| Source note | Borylation dataset from Roche |
|---|
