Dimethylformamide → 1-(Allyloxy)-2-chloro-5-nitrobenzene

HRID 1638913Notes

Reaction equation

HRID 1638913 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 128819301-(Allyloxy)-2-chloro-5-nitrobenzene

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-f816798a8c764ad9be95c840296571e5
Source dataset
uspto-grants-1989_11
Patent number
US04881967

Reaction notes

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