4-Methoxybenzaldehyde → 1-(2-Chloro-2-nitrovinyl)-4-methoxybenzene

HRID 1926899Notes

Reaction equation

HRID 1926899 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.Br[CH2:12][N+:13]([O-:15])=[O:14].[Cl-:16].C[NH2+]C.[F-].[K+]>C1(C)C(C)=CC=CC=1.ClCCl.O>[Cl:16]/[C:12](/[N+:13]([O-:15])=[O:14])=[CH:7]\[C:6]1[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1

Participants

8

Reactant 4

HCID 312444-MethoxybenzaldehydeHCID 68423BromonitromethaneHCID 522689Potassium FluorideHCID 12954980Dimethylazanium;chloride

Product 1

HCID 58207481-(2-Chloro-2-nitrovinyl)-4-methoxybenzene

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolventHCID 7237O-XyleneSolvent

Procedure

As in a procedure described in the literature [D. Dauzonne, Synthesis, 1990, 66-70], stir a mixture of 10.0 g (73.5 mmol) 4-methoxybenzaldehyde, 9.0 ml (13.5 g, 96.2 mmol) bromonitromethane, 53.9 g (661.0 mmol) dimethylammonium chloride and 0.6 g (1.0 mmol) potassium fluoride in 150 ml xylene on a water separator at 160° C. for 15 hours. After adding 25 ml water and 100 ml dichloromethane, separate the organic phase and extract the aqueous phase three times with 100 ml dichloromethane each time. Dry the combined organic extracts over sodium sulphate, filter and concentrate by vacuum evaporation. Chromatograph the residue on silica gel (solvent: cyclohexane/dichloromethane 1:1). 9.6 g (59% of theor.) of the target compound is obtained.

Workup

  1. customAs in a procedure described in the literature [D. Dauzonne, Synthesis, 1990, 66-70]
  2. customseparate the organic phase
  3. extractionextract the aqueous phase three times with 100 ml dichloromethane each time
  4. dry with materialDry the combined organic extracts over sodium sulphate
  5. filtrationfilter
  6. concentrationconcentrate by vacuum evaporation
  7. custom9.6 g (59% of theor.) of the target compound is obtained

Sources & evidence

ORD record
ord-56987c0d79654ba9af5c7415de26a595
Source dataset
uspto-grants-2012_05
Patent number
US08183246B2

Reaction notes

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