Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Trimethyl borate | HCID 8470 | — |
| Reactant | Benzene, 1-bromo-4-(2-propenyl)- | HCID 137529 | — |
| Reactant | Magnesium | HCID 5462224 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 54555650 | HCID 54555650 | 65.8% |
Reaction Steps
To a mixture comprising sufficiently dried metal magnesium (120 mmol) and 30 ml of tetrahydrofuran (hereinafter referred to as THF), was gradually added a solution of 120 mmol of the 4-allyl-bromobenzene in 200 ml of THF to prepare a Grignard reagent. To this reagent was added dropwise a solution of trimethyl borate (120 mmol) in 100 ml of THF at a temperature not exceeding -65° C., stirred for a whole day and night. Subsequently, the mixture was kept at 0° C., 200 ml of 10% hydrochloric acid was gradually added thereto at the same temperature, and then the reaction mixture was stirred for 30 min. The mixture thus obtained was extracted twice with 500 ml of diethyl ether, the organic layer was washed with a saturated brine solution, and then the solvent was removed under a reduced pressure. The residue was sufficiently washed with 500 ml of heptane and then dried to obtain 4-allylphenyl boric acid (79 mmol).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05879585 |
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| Source dataset | uspto-grants-1999_03 |
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| ORD ID | ord-7b079be9e50d49d38da6f39a4ba25980 |
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| Source note | uspto-grants-1999_03 |
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