HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → Dimethyl 2'-methoxybiphenyl-3,5-dicarboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1,3-Benzenedicarboxylic acid, 5-bromo-, 1,3-dimethyl ester | HCID 103954 | — |
| Reactant | 2-Methoxyphenylboronic acid | HCID 2733958 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Solvent | Isopropanol | HCID 3776 | — |
| Product | Dimethyl 2'-methoxybiphenyl-3,5-dicarboxylate | HCID 59569648 | — |
Reaction Steps
To dimethyl 5-bromoisophthalate (1.5 g, 5.5 mmol, Aldrich) in i-PrOH (33.3 ml) and water (16.7 ml), 2-methoxy phenyl boronic acid (Aldrich), triethyl amine (841 mg, 8.25 mmol) and PdCl2(dppf) (180 mg, 0.22 mmol) were added and the reaction mixture was refluxed for 4 h. Then reaction mixture was diluted with ether, washed with water, brine and dried. Volatiles were removed under vacuum and the crude residue was column chromatographed (30% ethylacetate/70% hexanes) to yield 650 mg of dimethyl 2′-methoxybiphenyl-3,5-dicarboxylate as white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08299267B2 |
| Source dataset | uspto-grants-2012_10 |
| ORD ID | ord-82a3e1f01ecb4aeab26c1836fa42792e |
| Source note | uspto-grants-2012_10 |