Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Toluene | HCID 1140 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | 2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl | HCID 11269872 | — |
| Reactant | Methyl 3-bromo-4-(tert-butyl)benzoate | HCID 11959028 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Product | HCID 57672475 | HCID 57672475 | 39% |
Reaction Steps
A mixture of methyl 3-bromo-4-tert-butylbenzoate (120 mg, 443 μmol), compound C.3 (226 mg, 664 μmol), potassium phosphate (282 mg, 1328 μmol), 2-(dicyclohexylphosphino)-2′,6′-dimethoxy-1,1′-biphenyl (36 mg, 89 μmol) (Aldrich, CAS# 657408-07-6), and tris(dibenzylideneacetone)dipalladium(0) (20 mg, 22 μmol) in toluene (1.0 mL) was stirred overnight at 110° C. The mixture was cooled to room temperature, filtered through a pad of celite with EtOAc rinsings, and concentrated. The crude product was purified by silica gel flash chromatography (0-10% EtOAc/hexane) to afford compound C.4 (63 mg, 39% yield) as a colorless oil. MS ESI (pos.) m/e: 388 (M+H2O), 393 (M+Na).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07572934B2 |
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| Source dataset | uspto-grants-2009_08 |
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| ORD ID | ord-709066a29d5249e5935fccfd4e5765d9 |
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| Source note | uspto-grants-2009_08 |
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