Allyl bromide → 3-Allyloxy-4-bromoanisol

HRID 1464692Notes

Reaction equation

HRID 1464692 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[OH:10].C(=O)([O-])[O-].[K+].[K+].[CH2:17](Br)[CH:18]=[CH2:19]>CC#N>[CH2:19]([O:10][C:3]1[CH:4]=[C:5]([O:8][CH3:9])[CH:6]=[CH:7][C:2]=1[Br:1])[CH:18]=[CH2:17]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 134938392-Bromo-5-methoxyphenol

Product 1

HCID 147034223-Allyloxy-4-bromoanisolYield 111%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-bromo-3-hydroxyanisol (14.49, 59.3 mmol), synthesized by known methods, in CH3CN (200 ml), dry potassium carbonate (20 g) and allylbromide (8.0 ml, 92.4 mmol) was added. The reaction mixture was stirred and refluxed for 1 hour and thereafter cooled to room temperature, filtered and evaporated. The residue was dissolved in ether and extracted with water. The organic layer was separated and dried (Na2SO4). Evaporation of the solvent afforded 16.0 g (93%) of 3-allyloxy-4-bromoanisol as an oil. GC/MS (HP-5970A) m/e=244 (40) M+ and M+ -1 at m/e=242 (40), 163 (100), 149 (97), 135 (62).

Workup

  1. temperaturerefluxed for 1 hour
  2. filtrationfiltered
  3. customevaporated
  4. dissolutionThe residue was dissolved in ether
  5. extractionextracted with water
  6. customThe organic layer was separated
  7. dry with materialdried (Na2SO4)
  8. customEvaporation of the solvent

Sources & evidence

ORD record
ord-b51aa913910342a8b842f3b306dd0416
Source dataset
uspto-grants-1994_04
Patent number
US05306830

Reaction notes

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