Boron tribromide → 3-Fluoro-4-hydroxybenzonitrile

HRID 626130

Reaktionsgleichung

Reaktionsgleichung von HRID 626130
B(Br)(Br)Br.[F:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][C:13]=1[O:14]C)[C:9]#[N:10]>ClCCl>[F:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][C:13]=1[OH:14])[C:9]#[N:10]

Komponenten

4

Edukt 2

HCID 25134Boron tribromideHCID 27745483-Fluoro-4-methoxybenzonitrile

Produkt 1

HCID 27829443-Fluoro-4-hydroxybenzonitrileAusbeute 94,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

BBr3 (20 mL, 0.211 mol) was added to 3-fluoro-4-methoxybenzonitrile (15.6 g, 0.103 mol) in dichloromethane (100 mL) at 0° C. The mixture was refluxed for 3 days under a nitrogen atmosphere. The reaction mixture was quenched with ice water and extracted with dichloromethane. The organic layer was washed with water and brine and then dried over sodium sulfate. Solvent evaporation under reduced pressure gave 13.3 g (94%) of the product as a gray solid. 1H NMR (400 MHz, CDCl3) δ 7.38-7.42 (m, 2H), 7.09 (dd, J=8.8 Hz, 8.4 Hz, 1H), 5.68 (s, 1H).

Aufarbeitung

  1. temperatureThe mixture was refluxed for 3 days under a nitrogen atmosphere
  2. customThe reaction mixture was quenched with ice water
  3. extractionextracted with dichloromethane
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. customSolvent evaporation under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-dfd4485801a74d3e95fec146c510a0fd
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309211B2

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