HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1914039Generated: October 29, 2026
1,3-Dibromobenzene → HCID 71138690, compound
https://huagongshe.com/reaction/1914039
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 1,3-Dibromobenzene | HCID 7927 | — |
| Reactant | Binap, (A+-)- | HCID 634876 | — |
| Reactant | 8-Oxa-3-azabicyclo[3.2.1]octane | HCID 12069231 | — |
| Reactant | Sodium t-butoxide | HCID 23676156 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 71138690 | HCID 71138690 | 67.3% |
Reaction Steps
A mixture of 1,3-dibromobenzene (242 μL, 2.00 mmol), 8-oxa-3-azabicyclo[3.2.1]octane (226 mg, 2.00 mmol), Pd2(dba)3 (45.8 mg, 0.0500 mmol), rac-BINAP (96.3 mg, 0.150 mmol) and NaOtBu (231 mg, 2.40 mmol) in toluene was heated at 80° C. for 13 hours under nitrogen. After cooling to room temperature, the mixture was diluted with DCM and filtered through a Celite pad. The combined filtrate and washings were concentrated. The residue was purified by silica gel column chromatography (EtOAc/hexane=9:1) to afford desired product (361 mg, 67.3%) as colorless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08609688B2 |
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| Source dataset | uspto-grants-2013_12 |
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| ORD ID | ord-2d4c154df52341cfabc3687646c7f675 |
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| Source note | uspto-grants-2013_12 |
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