HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1852920Generated: November 1, 2026
1,3-Dibromobenzene → HCID 71138448, compound
https://huagongshe.com/reaction/1852920
Participants
| Role | Name | HCID | Charge |
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| Reactant | 1,3-Dibromobenzene | HCID 7927 | — |
| Reactant | Binap, (A+-)- | HCID 634876 | — |
| Reactant | 2,6-Dimethylmorpholine, cis- | HCID 641500 | — |
| Reactant | Sodium t-butoxide | HCID 23676156 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 71138448 | HCID 71138448 | 65.9% |
Reaction Steps
A mixture of 1,3-dibromobenzene (242 μL, 2.00 mmol), cis-2,6-dimethylmorpholine (248 μL, 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 11 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=98:2→97:3) to afford desired product (356 mg, 65.8%) as pale yellow oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08962619B2 |
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| Source dataset | uspto-grants-2015_02 |
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| ORD ID | ord-53ea3806424f422897361ab4e6fa30fb |
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| Source note | uspto-grants-2015_02 |
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