Sodium Hydroxide → 5-Bromo-7-fluoro-2-[2-fluoro-4-(methylsulfonyl)phenyl]benzo[d]oxazole

HRID 710089Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 710089
[NH2:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[C:4]([F:9])[C:3]=1[OH:10].[F:11][C:12]1[CH:20]=[C:19]([S:21]([CH3:24])(=[O:23])=[O:22])[CH:18]=[CH:17][C:13]=1[C:14](O)=O.[OH-].[Na+]>CCOC(C)=O.O>[Br:8][C:6]1[CH:5]=[C:4]([F:9])[C:3]2[O:10][C:14]([C:13]3[CH:17]=[CH:18][C:19]([S:21]([CH3:24])(=[O:22])=[O:23])=[CH:20][C:12]=3[F:11])=[N:1][C:2]=2[CH:7]=1

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 27376372-Amino-4-bromo-6-fluorophenolHCID 283559322-Fluoro-4-(methylsulphonyl)benzoic acid

Produkt 1

HCID 712573005-Bromo-7-fluoro-2-[2-fluoro-4-(methylsulfonyl)phenyl]benzo[d]oxazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 22728543Water ethylacetateLösungsmittel

Reaktionsbedingungen

Temperatur
195 °C

Versuchsvorschrift

2-Amino-4-bromo-6-fluorophenol (2.6 g, 9.7 mmol) and 2-fluoro-4-(methylsulfonyl)benzoic acid (2.1 g, 9.7 mmol) were dissolved in polyposphoric acid (63.5 g). This mixture was heated at 195° C. for three and half hours. Reaction mixture cooled to rt and diluted with ice water (100 ml). Aqueous layer basified with sodium hydroxide pellets to pH 9. Work up (EtOAc/H2O) followed by evaporation of EtOAc afforded the crude. Crude (3.1 g) was used in the next step without further purification.

Aufarbeitung

  1. customReaction mixture
  2. temperaturecooled to rt
  3. customfollowed by evaporation of EtOAc
  4. customafforded the crude
  5. customCrude (3.1 g) was used in the next step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-92f53721d5b14bfabd6dd4f27220cb63
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181214B2

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