Phosphorus pentachloride → N-(4-bromophenyl)-2-chloro-6-fluorobenzenecarbohydrazonoyl chloride

HRID 508711

Reaktionsgleichung

Reaktionsgleichung von HRID 508711
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8]/[N:9]=[CH:10]/[C:11]2[C:16]([F:17])=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:18])=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:20]>C1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][N:9]=[C:10]([Cl:20])[C:11]2[C:16]([F:17])=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:18])=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 24819Phosphorus pentachlorideHCID 900336584-bromo-N-[(E)-(2-chloro-6-fluorophenyl)methylideneamino]aniline

Produkt 1

HCID 131733232N-(4-bromophenyl)-2-chloro-6-fluorobenzenecarbohydrazonoyl chlorideAusbeute 23 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

To a solution of (2E)-1-(4-bromophenyl)-2-(2-chloro-6-fluorobenzylidene)hydrazine (0.300 g, 1.32 mmol) in benzene (10 mL) was added PCl5 (0.330 g, 1.58 mmol). The reaction mixture was stirred at RT for 18 h. The reaction mass was quenched in water, neutralized with NaHCO3 and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulphate and concentrated to afford 0.110 g of the desired product. 1H NMR (300 MHz, DMSO d6): δ 7.17 (d, J=8.7 Hz, 2H), 7.41 (d, J=8.7 Hz, 3H), 7.45-7.61 (m, 2H), 10.26 (s, 1H). MS (m/z): 361.34 (M−H)−.

Aufarbeitung

  1. customThe reaction mass was quenched in water
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-5b2edc6d26a5453f91b3692a8370b870
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096545B2

Verknüpfte Notizen

Wird geladen…