Dimethylformamide → HCID 12881930, compound

HRID 344590Notes

Reaction equation

HRID 344590 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[OH:11].[CH2:12](Br)[CH:13]=[CH2:14].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH2:14]([O:11][C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[Cl:1])[CH:13]=[CH2:12]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 692642-Chloro-5-nitrophenol

Product 1

HCID 12881930HCID 12881930, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 7.4 g of 2-chloro-5-nitrophenol, 5.4 g of allyl bromide, 5.9 g of anhydrous potassium carbonate and 50 mL of dry N,N-dimethylformamide (DMF) was stirred at room temperature over a weekend. Then the mixture was poured into water, and the resulting mixture was extracted twice with ethyl acetate and twice with ether. The combined extracts were washed with water, then with brine, dried (Na2SO4), filtered and stripped of the solvents. The residue was recrystallized from hexane to give 1-(allyloxy)-2-chloro-5-nitrobenzene (3A), as orange needles, m.p.: 58°-59.5° C.

Workup

  1. extractionthe resulting mixture was extracted twice with ethyl acetate and twice with ether
  2. washThe combined extracts were washed with water
  3. dry with materialwith brine, dried (Na2SO4)
  4. filtrationfiltered
  5. customThe residue was recrystallized from hexane

Sources & evidence

ORD record
ord-97341458490142598bf2df507ff4f64f
Source dataset
uspto-grants-1991_10
Patent number
US05053071

Reaction notes

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