Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Hexane | HCID 8058 | — |
| Reactant | Trimethyl borate | HCID 8470 | — |
| Reactant | Butyllithium | HCID 178418339 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 16732350 | HCID 16732350 | 79% |
Reaction Steps
Into 200 ml of dehydrated THF, tetrahydrofuran, 20 g of 7-bromobenzanthracene obtained above was dissolved, and the obtained solution was cooled at −62° C. To the cooled solution, 50 ml of a 1.6 M hexane solution of normal-butyllithium was added dropwise, and the resultant mixture was stirred for 30 minutes. The temperature was raised to −5° C. and then lowered to −64° C. To the cooled fluid, a THF solution of 22.4 g of trimethyl borate was added dropwise. After one night, the reaction fluid was adjusted at the acidic condition with a dilute hydrochloric acid, treated by extraction with toluene and washed with water and a saturated aqueous solution of sodium chloride, and the organic layer was dried with anhydrous sodium sulfate. After the solvent was removed by distillation, the obtained residue was crystallized from toluene/hexane, and 14 g of 7-benzanthraceneboronic acid was obtained as cream crystals (the yield: 79%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07829206B2 |
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| Source dataset | uspto-grants-2010_11 |
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| ORD ID | ord-db1013e5980a4718945b1a97b980a1a3 |
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| Source note | uspto-grants-2010_11 |
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