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

HRID 861276Notes

Reaction equation

HRID 861276 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-3201197abe1c41aa838a9a0c222c6531
Source dataset
uspto-grants-1998_02
Patent number
US05714304

Reaction notes

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