5-Bromo-2-nitrobenzaldehyde → HCID 178469011, compound

HRID 2075172Notes

Reaction equation

HRID 2075172 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[CH:7]=O.[NH2:13][C:14]1[CH:24]=[CH:23][C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:16][C:15]=1[F:25]>C(O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)/[CH:7]=[N:13]/[C:14]1[CH:24]=[CH:23][C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:16][C:15]=1[F:25]

Participants

4

Reactant 2

HCID 972335-Bromo-2-nitrobenzaldehydeHCID 20536493Ethyl 4-amino-3-fluorobenzoate

Product 1

HCID 178469011HCID 178469011, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-bromo-2-nitrobenzaldehyde (2.79 g, 12.13 mmol) and ethyl 4-amino-3-fluorobenzoate (2.22 g, 12.12 mmol) in ethanol (60 mL) was stirred at reflux for 2 h. After the solvent was removed under reduced pressure, the reaction mixture was purified by silica gel column chromatography to give (E)-ethyl 4-(5-bromo-2-nitrobenzylideneamino)-3-fluorobenzoate as pale yellow solid: 1H NMR (400 MHz, CDCl3) δ 9.01 (s, 1H), 8.47 (d, J=2.0 Hz, 1H), 8.02 (d, J=8.6 Hz, 1H), 7.91 (dd, J=1.6, 2.3, 9.0 Hz, 1H), 7.85 (dd, J=1.6, 11.0 Hz, 1H), 7.80 (dd, J=2.3, 8.6 Hz, 1H), 7.24 (t, J=8.0 Hz, 1H), 4.40 (q, J=7.0 Hz, 2H), 1.42 (t, J=7.0 Hz, 3H); 19F NMR (376 MHz, CDCl3) δ −125.6.

Workup

  1. temperatureat reflux for 2 h
  2. customAfter the solvent was removed under reduced pressure
  3. customthe reaction mixture was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-dfefb667d6ac4efb86676ad059b43bca
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Reaction notes

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