HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → Methyl 4'-hydroxy-3',5'-dimethylbiphenyl-4-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Methyl 4-bromobenzoate | HCID 12081 | — |
| Reactant | 2,6-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol | HCID 2734649 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | Methyl 4'-hydroxy-3',5'-dimethylbiphenyl-4-carboxylate | HCID 57747356 | 79.1% |
Reaction Steps
A solution of 2,6-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (525 mg, 2.12 mmol), methyl 4-bromobenzoate (460 mg, 2.14 mmol), PdCl2(dppf) (80 mg, 0.11 mmol) and Cs2CO3 (1.40 g, 4.31 mmol) in DMF (10 mL, 5% H2O) was heated at 80° C. for 1 h. The reaction mixture was diluted with EtOAc (50 mL), washed with H2O (2×50 mL), and dried over Na2SO4. Purification on a silica gel column gave the desired product as a pale yellow solid (430 mg). NMR (CDCl3): δ 8.08 (d, 2H), 7.62 (d, 2H), 7.29 (s, 2H), 4.75 (s, 1H), 3.95 (s, 3H), 2.35 (s, 6H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08207178B2 |
| Source dataset | uspto-grants-2012_06 |
| ORD ID | ord-a99bbe64883849d3a055f9f4c1cdcac1 |
| Source note | uspto-grants-2012_06 |