Allyl bromide → 4-Allyloxy-2,5-dichloronitrobenzene

HRID 1957471Notes

Reaction equation

HRID 1957471 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([Cl:11])=[CH:4][C:3]=1[OH:12].C(=O)([O-])[O-].[K+].[K+].[CH2:19](Br)[CH:20]=[CH2:21]>C(#N)C>[CH2:21]([O:12][C:3]1[C:2]([Cl:1])=[CH:7][C:6]([N+:8]([O-:10])=[O:9])=[C:5]([Cl:11])[CH:4]=1)[CH:20]=[CH2:19]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 221082,5-Dichloro-4-nitrophenol

Product 1

HCID 190676764-Allyloxy-2,5-dichloronitrobenzeneYield 93.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The product of step (a) (59.3 g, 285 mmol), 550 ml acetonitrile, 43 g (314 mmol) of potassium carbonate and 27.2 ml (314 mmol) of allyl bromide were combined and heated to reflux, and then the reaction was evaporated under reduced pressure. The mixture was extracted with diethyl ether, washed with water, and separated. The organics were dried over magnesium sulfate and stripped to yield 66.1 g of 4-allyloxy-2,5-dichloronitrobenzene product.

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. customthe reaction was evaporated under reduced pressure
  4. extractionThe mixture was extracted with diethyl ether
  5. washwashed with water
  6. customseparated
  7. dry with materialThe organics were dried over magnesium sulfate

Sources & evidence

ORD record
ord-b1d3a2b801a248e68ada93e3f0958bd5
Source dataset
uspto-grants-1998_07
Patent number
US05786301

Reaction notes

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