Hydrogen Bromide → 4-Bromo-2-fluoro-3-methylbenzonitrile

HRID 717190

Reaktionsgleichung

Reaktionsgleichung von HRID 717190
N([O-])=O.[K+].N[C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[C:8]([F:14])[C:7]=1[CH3:15].[BrH:16].[OH-].[Na+]>CS(C)=O.[Cu]Br.O>[Br:16][C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[C:8]([F:14])[C:7]=1[CH3:15]

Komponenten

8

Edukt 4

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 516910Potassium nitrite2×HCID 450786764-Amino-2-fluoro-3-methylbenzonitrile

Produkt 1

HCID 595569134-Bromo-2-fluoro-3-methylbenzonitrileAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24593copper(I) bromideKatalysatorHCID 679Dimethyl SulfoxideLösungsmittel2×HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of dimethyl sulfoxide (400 mL) and potassium nitrite (22.67 g, 266 mmol) was stirred to dissolve potassium nitrite and 4-amino-2-fluoro-3-methylbenzonitrile (10 g, 66.6 mmol) and copper(I) bromide (1.911 g, 13.32 mmol) were added. Aqueous 48% hydrogen bromide (33 mL, 266 mmol), diluted with dimethyl sulfoxide (200 mL), was added dropwise and the reaction stirred for 2 h. After complete conversion of starting material, the reaction mixture was poured into iced-cold water and neutralized to pH 7 with cold concentrated sodium hydroxide. The resulting solid was collected by filtration to give the desired product (11.4 g, 53.3 mmol, 80% yield) as white solid. 1H NMR (400 MHz, CHLOROFORM-d) δ (ppm) 7.47 (d, J=9.37 Hz, 1H), 7.33 (t, 1H), 2.39 (d, J=2.34 Hz, 3H).

Aufarbeitung

  1. additionwere added
  2. additionwas added dropwise
  3. stirringthe reaction stirred for 2 h
  4. filtrationThe resulting solid was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-7d6b1d4bcca846e3a034e199c25559e6
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09193692B2

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