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

HRID 59223

Reaction equation

HRID 59223 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 900336584-bromo-N-[(E)-(2-chloro-6-fluorophenyl)methylideneamino]anilineYield 31.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-711f195bc98643a6be7af84972bc0651
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Linked notes

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