Allyl bromide → 2-(Allyloxy)-4-fluoro-1-nitrobenzene

HRID 450035Notes

Reaction equation

HRID 450035 reaction equation
[CH2:1](Br)[CH:2]=[CH2:3].[F:5][C:6]1[CH:7]=[CH:8][C:9]([N+:13]([O-:15])=[O:14])=[C:10]([OH:12])[CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:1]([O:12][C:10]1[CH:11]=[C:6]([F:5])[CH:7]=[CH:8][C:9]=1[N+:13]([O-:15])=[O:14])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 99375-Fluoro-2-nitrophenolHCID 11430Potassium Carbonate

Product 1

HCID 197026902-(Allyloxy)-4-fluoro-1-nitrobenzeneYield 75%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Allyl bromide (3.4 g, 28 mmol, 1.5 eq) was added to a mixture of 5-fluoro-2-nitro-phenol (3.0 g, 19 mmol, 1 eq) and potassium carbonate (5.2 g, 38 mmol, 2 eq) in anhydrous acetonitrile (25 ml) and the mixture was heated to reflux for 6 hr. The reaction mixture was filtered and washed with acetonitrile and the filtrate concentrated to dryness to give 2-allyloxy-4-fluoro-1-nitro-benzene (2.8 g, 75%). The crude compound was used in the next stage without purification.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 6 hr
  3. filtrationThe reaction mixture was filtered
  4. washwashed with acetonitrile
  5. concentrationthe filtrate concentrated to dryness

Sources & evidence

ORD record
ord-52b7813c35a64f8c9e1c53600ff0b7e6
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Reaction notes

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