HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanol → 4-Bromo-2-fluoro-6-methoxybenzonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Sodium bis(trimethylsilyl)amide | HCID 2724254 | — |
| Reactant | 4-Bromo-2,6-difluorobenzonitrile | HCID 2756916 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Sodium chloride; water | HCID 57417360 | — |
| Product | 4-Bromo-2-fluoro-6-methoxybenzonitrile | HCID 57442209 | — |
Reaction Steps
To methanol (0.28 mL, 6.9 mmol) and 4-bromo-2,6-difluorobenzonitrile (1500 mg, 6.88 mmol) in THF (34 mL) was added NaHMDS (6.88 mL, 1.0 M in THF, 6.88 mmol) at 0° C. The reaction mixture was stirred at rt overnight, and diluted with brine, extracted with EtOAc. The organic layer was dried, and evaporated. The crude product was purified by column chromatography (0-30% EtOAc/Hex) to give 4-bromo-2-fluoro-6-methoxybenzonitrile.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09206199B2 |
| Source dataset | uspto-grants-2015_12 |
| ORD ID | ord-034cdd84f10f43d5b1f09f17125f0487 |
| Source note | uspto-grants-2015_12 |