Potassium Carbonate → HCID 59520007, compound

HRID 1162079Notes

Reaction equation

HRID 1162079 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:11]([O-:13])=[O:12])C(O)=C([CH:9]=1)C=O.Br[CH:15]([C:21]([O:23][CH2:24][CH3:25])=O)[C:16]([O:18][CH2:19][CH3:20])=[O:17].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[Br:1][C:2]1[CH:3]=[C:4]([N+:11]([O-:13])=[O:12])[C:24]2[O:23][CH:21]=[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:25]=2[CH:9]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 69637Diethyl bromomalonateHCID 6186995-Bromo-2-hydroxy-3-nitrobenzaldehyde

Product 1

HCID 59520007HCID 59520007, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 5-bromo-2-hydroxy-3-nitrobenzaldehyde (8.9 g, 36.2 mmol), diethyl bromomalonate (6.3 mL, 37.3 mmol) and potassium carbonate (4.6 g) in butanone (50 mL) was heated a reflux for 4 h. The mixture was cooled, filtered and evaporated to give the crude product which was recrystallized from ethanol. Yield: 6.6 g (58%) of a pale yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.29 (t, J=7.0 Hz, 3H) 4.35 (q, J=7.1 Hz, 2H) 7.83 (s, 1H) 8.39 (d, J=2.0 Hz, 1H) 8.43 (d, J=2.0 Hz, 1H).

Workup

  1. temperaturewas heated
  2. temperaturea reflux for 4 h
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-cbb022fb54f64b339cd997ab4c3098f8
Source dataset
uspto-grants-2010_10
Patent number
US07820675B2

Reaction notes

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