Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Trimethyl borate | HCID 8470 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | HCID 66691631 | HCID 66691631 | — |
| Reactant | Butyllithium | HCID 178418339 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 66692124 | HCID 66692124 | 58% |
Reaction Steps
To a solution of 6.00 g (16.6 mmol) [(2-bromo-5-fluorobenzyl)oxy](triisopropyl)silane which was prepared according to intermediate example 299c in 60 mL tetrahydrofuran were added 7.31 mL n-butyllithium (2.5M in hexane) at −78° C. After 20 minutes of stirring 5.58 mL trimethyl borate were added and stirring was continued for additional 60 minutes. The mixture was allowed to warm to 23° C., poured into a saturated ammonium chloride solution and extracted with ethyl acetate. The organic layer was washed with brine and dried over sodium sulfate. After filtration and removal of the solvent the residue was purified by chromatography to give 3.16 g (58%) of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09255100B2 |
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| Source dataset | uspto-grants-2016_02 |
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| ORD ID | ord-1483295540d04e1e9b9efd3362b2f893 |
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| Source note | uspto-grants-2016_02 |
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