HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → Ethyl 2'-methyl[1,1'-biphenyl]-3-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | Ethyl 3-bromobenzoate | HCID 90488 | — |
| Reactant | 2-Methylphenyl boronic acid | HCID 2733267 | — |
| Reactant | 4'-Methyl-biphenyl-3-carboxylic acid ethyl ester | HCID 10728754 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | Ethyl 2'-methyl[1,1'-biphenyl]-3-carboxylate | HCID 12853045 | — |
Reaction Steps
2′-Methyl-biphenyl-3-carboxylic acid ethyl ester was synthesized as described for 4′-methyl-biphenyl-3-carboxylic acid ethyl ester. Ethyl 3-bromobenzoate (8.02 g, 35.03 mmol, 1 eq.) and o-tolylboronic acid (5.0 g, 36.78 mmol, 1.05 eq.) in THF were treated with aqueous 2M sodium carbonate (38.5 mL, 77.07 mmol, 2.2 eq.), palladium(II) acetate (0.79 g, 3.50 mmol, 10 mol %), triphenylphosphine (4.04 g, 15.40 mmol, 4.4×Pd), and copper(I) iodide (0.22 g, catalyst). When complete, the reaction was worked up as described leaving a dark brown oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07132456B2 |
| Source dataset | uspto-grants-2006_11 |
| ORD ID | ord-bd5da445a8064ef199454b371e0862a1 |
| Source note | uspto-grants-2006_11 |