HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → Methyl 2',4'-difluoro-3-isopropoxybiphenyl-4-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 2,4-Difluorophenylboronic acid | HCID 2734334 | — |
| Reactant | 2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl | HCID 11269872 | — |
| Reactant | Methyl 4-iodo-2-isopropoxybenzoate | HCID 90422834 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | Methyl 2',4'-difluoro-3-isopropoxybiphenyl-4-carboxylate | HCID 117992133 | 99.4% |
Reaction Steps
A mixture of methyl 4-iodo-2-isopropoxybenzoate (4.10 g), (2,4-difluorophenyl)boronic acid (4.04 g), dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (0.789 g), a 2 M aqueous sodium carbonate solution (19.2 mL), tris(dibenzylideneacetone)dipalladium(0) (0.821 g), and toluene (50 mL) was stirred at 100° C. for 2 hours in an argon atmosphere. The reaction mixture was allowed to cool to room temperature. Then, the organic layer was separated and passed through a short silica gel (NH) column, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound (3.90 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09353108B2 |
| Source dataset | uspto-grants-2016_05 |
| ORD ID | ord-d2ec24ade8614775a9d783159eb23810 |
| Source note | uspto-grants-2016_05 |