Reaktion #87501

Reaktionsgleichung

2-chloro-6-fluorobenzaldehyde

(4-bromophenyl)hydrazine

NaHCO3

→

desired product

Ausbeute 31.4%

(2E)-1-(4-bromophenyl)-2-(2-chloro-6-fluorobenzylidene) hydrazine

Ausbeute 31.4%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction mass was quenched in water
2. 2
   Extraktionextracted with ethyl acetate
3. 3
   TrocknenThe organic layer was dried over anhydrous sodium sulphate
4. 4
   Einengenconcentrated
5. 5
   SonstigeThe obtained crude product
6. 6
   Sonstigewas purified by column chromatography on silica gel
7. 7
   Wascheneluting with 4.6% EA

Vorschrift

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)+.

Quelle