1-Chloro-2,4-Dinitrobenzene → HCID 10163434, compound

HRID 1743223Notes

Reaction equation

HRID 1743223 reaction equation
[H-].[Na+].[CH:3]([C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[C:16]3[C:17]([CH3:24])=[C:18]([OH:23])[C:19]([CH3:22])=[C:20]([CH3:21])[C:15]=3[O:14][C:13]2([CH3:26])[CH3:25])=[CH:8][CH:7]=1)([CH3:5])[CH3:4].Cl[C:28]1[CH:33]=[CH:32][C:31]([N+:34]([O-:36])=[O:35])=[CH:30][C:29]=1[N+:37]([O-:39])=[O:38].O>CN(C)C=O>[CH:3]([C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[C:16]3[C:17]([CH3:24])=[C:18]([O:23][C:32]4[CH:33]=[CH:28][C:29]([N+:37]([O-:39])=[O:38])=[CH:30][C:31]=4[N+:34]([O-:36])=[O:35])[C:19]([CH3:22])=[C:20]([CH3:21])[C:15]=3[O:14][C:13]2([CH3:26])[CH3:25])=[CH:8][CH:7]=1)([CH3:5])[CH3:4]

Participants

6

Reactant 4

HCID 61-Chloro-2,4-DinitrobenzeneHCID 962WaterHCID 24758Sodium hydrideHCID 10881888HCID 10881888, compound

Product 1

HCID 10163434HCID 10163434, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% liquid paraffin dispersion, 270 mg, 6.75 mmol) was added to a solution of 3-(4-isopropylphenyl)-2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran-5-ol (2.0 g, 6.16 mmol) in N,N-dimethylformamide (30 mL) at 0° C., and the mixture was stirred for 20 minutes at the same temperature. To the reaction mixture was added 1-chloro-2,4-dinitrobenzene (1.37 g, 6.78 mmol) and the mixture was stirred for 20 minutes at room temperature. The reaction mixture was poured into water (50 mL), and extracted twice with ethyl acetate. The organic layers were combined, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was crystallized from ethyl acetate-hexane to obtain the title compound (1.5 g, yield 50%).

Workup

  1. stirringthe mixture was stirred for 20 minutes at room temperature
  2. extractionextracted twice with ethyl acetate
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-9355c45d3d97425597bb027886283d80
Source dataset
uspto-grants-2006_03
Patent number
US07008950B1

Reaction notes

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