HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-Methyl-4-methoxycarbonylphenylboronic acid, pinacol ester → 4-(6,6-Dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-3-methyl-benzoic acid methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-Methyl-4-methoxycarbonylphenylboronic acid, pinacol ester | HCID 11087024 | — |
| Reactant | 6,6-Dimethyl-bicyclo[3.1.1]hept-2-en-2-yl trifluoromethanesulfonate | HCID 22219693 | — |
| Product | 4-(6,6-Dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-3-methyl-benzoic acid methyl ester | HCID 69652515 | 69.5% |
Reaction Steps
3-Methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester of Example 28, Step A (1.00 g, 3.62 mmol) and 6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-yl trifluoromethanesulfonate (1.17 g, 4.34 mmol) were reacted in the manner of Example 1, Step F. Purification by flash column chromatography on silica gel, eluting with a solvent gradient of from 0 to 5% ethyl acetate in hexane, afforded the title compound (0.680 g) as a light yellow oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07022699B2 |
| Source dataset | uspto-grants-2006_04 |
| ORD ID | ord-3e0bd9e391ec4410a11aee9176336aed |
| Source note | uspto-grants-2006_04 |