4-Bromophenylhydrazine → 4-bromo-N-[(E)-(2-chloro-6-fluorophenyl)methylideneamino]aniline

HRID 59223

Reaktionsgleichung

Reaktionsgleichung von HRID 59223
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:3]=1[CH:4]=O.[Br:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][NH2:19])=[CH:14][CH:13]=1.C([O-])(O)=O.[Na+]>C(O)C>[Br:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18]/[N:19]=[CH:4]/[C:3]2[C:6]([F:10])=[CH:7][CH:8]=[CH:9][C:2]=2[Cl:1])=[CH:14][CH:13]=1

Komponenten

5

Edukt 3

HCID 121584-BromophenylhydrazineHCID 678472-Chloro-6-fluorobenzaldehydeHCID 516892Sodium Bicarbonate

Produkt 1

HCID 900336584-bromo-N-[(E)-(2-chloro-6-fluorophenyl)methylideneamino]anilineAusbeute 31,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 2-chloro-6-fluorobenzaldehyde (1.0 g, 6.32 mmol) in ethanol was added (4-bromophenyl)hydrazine (1.7 g, 7.59 mmol) and aq. solution of NaHCO3 (0.637 g, 4.59 mmol). The reaction mixture was stirred at RT for 5-6 h. The reaction mass was quenched in water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulphate and concentrated. The obtained crude product was purified by column chromatography on silica gel, eluting with 4.6% EA: pet. ether to afford 0.650 g of the desired product. 1H NMR (300 MHz, DMSO d6): δ 6.98 (d, J=7.8 Hz, 2H), 7.23-7.40 (m, 5H), 8.07 (s, 1H), 10.87 (br s, 1H). MS (m/z): 329.17 (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
  5. customThe obtained crude product
  6. customwas purified by column chromatography on silica gel
  7. washeluting with 4.6% EA

Quellen und Nachweise

ORD-Eintrag
ord-711f195bc98643a6be7af84972bc0651
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09439890B2

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