Hydrochloric Acid → 2-(Allyloxy)-4-fluoro-1-nitrobenzene

HRID 1656585Notes

Reaction equation

HRID 1656585 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([OH:8])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:18](Br)[CH:19]=[CH2:20].[O-]C1C=CC=CC=1.Cl>CC(C)=O.O>[CH2:20]([O:8][C:6]1[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=1[N+:9]([O-:11])=[O:10])[CH:19]=[CH2:18]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7841Allyl bromideHCID 99375-Fluoro-2-nitrophenolHCID 11430Potassium CarbonateHCID 119047Phenolate

Product 1

HCID 197026902-(Allyloxy)-4-fluoro-1-nitrobenzeneYield 100%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To 5-fluoro-2-nitrophenol (10 g, 63.6 mmol), which had been dissolved in 100 ml of acetone, was added potassium carbonate (16.6 g, 120 mmol). The pale yellow solution immediately turned bright red in color. Allyl bromide (15.4 g, 11.0 ml, 127 mmol) was added and the stirring was continued at room temperature. A thick red precipitate formed and 2 ml of distilled water was added to help dissolve the phenoxide salt. The round bottomed flask was then fitted with a condenser and the suspension was refluxed under a nitrogen atmosphere for 17 hours. The suspension was cooled to room temperature and 2N HCl was slowly added with stirring until all the solid had dissolved. The organics were extracted with ethyl acetate, washed with water and saturated aqueous sodium bicarbonate solution. The combined extracts were dried over magnesium sulphate, filtered and concentrated on the rotary evaporator and vacuum line to yield 2-(2-propenyloxy)-4-fluoronitrobenzene as an orange/yellow oil (12.5 g, 100%). This product was used in the next step without further purification.

Workup

  1. customwas continued at room temperature
  2. customA thick red precipitate formed
  3. customThe round bottomed flask was then fitted with a condenser
  4. temperaturethe suspension was refluxed under a nitrogen atmosphere for 17 hours
  5. dissolutionhad dissolved
  6. extractionThe organics were extracted with ethyl acetate
  7. washwashed with water and saturated aqueous sodium bicarbonate solution
  8. dry with materialThe combined extracts were dried over magnesium sulphate
  9. filtrationfiltered
  10. concentrationconcentrated on the rotary evaporator and vacuum line

Sources & evidence

ORD record
ord-c686011617334ae8b7851802c52cfe19
Source dataset
uspto-grants-1993_10
Patent number
US05254655

Reaction notes

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