Methanol → 4-Bromo-2-fluoro-6-methoxybenzonitrile

HRID 1502073Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1502073
[CH3:1][OH:2].[Br:3][C:4]1[CH:11]=[C:10](F)[C:7]([C:8]#[N:9])=[C:6]([F:13])[CH:5]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>C1COCC1.[Cl-].[Na+].O>[Br:3][C:4]1[CH:11]=[C:10]([O:2][CH3:1])[C:7]([C:8]#[N:9])=[C:6]([F:13])[CH:5]=1

Komponenten

6

Edukt 3

HCID 887MethanolHCID 2724254Sodium bis(trimethylsilyl)amideHCID 27569164-Bromo-2,6-difluorobenzonitrile

Produkt 1

HCID 574422094-Bromo-2-fluoro-6-methoxybenzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. extractionextracted with EtOAc
  2. customThe organic layer was dried
  3. customevaporated
  4. customThe crude product was purified by column chromatography (0-30% EtOAc/Hex)

Quellen und Nachweise

ORD-Eintrag
ord-034cdd84f10f43d5b1f09f17125f0487
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09206199B2

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