Allyl bromide → 4-(allyloxy)-3-bromobenzaldehyde

HRID 746333Notes

Reaction equation

HRID 746333 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[O:6].[CH2:11](Br)[CH:12]=[CH2:13].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH2:13][CH:12]=[CH2:11])[CH:5]=[O:6]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 763083-Bromo-4-hydroxybenzaldehyde

Product 1

HCID 27166134-(allyloxy)-3-bromobenzaldehyde

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3-Bromo-4-hydroxybenzaldehyde (20.1 g, 0.100 mol) and allyl bromide (14.5 g, 0.120 mol) were heated under reflux together with potassium carbonate (20.7 g, 0.150 mol) in 150 ml acetone (abs.) for 8 hours. After cooling, the solid was filtered off and washed with acetone. After complete concentration of the organic phase, there was obtained an oily residue that was used directly in the second step without further purification.

Workup

  1. temperatureAfter cooling
  2. filtrationthe solid was filtered off
  3. washwashed with acetone
  4. concentrationAfter complete concentration of the organic phase
  5. customthere was obtained an oily residue that
  6. customwas used directly in the second step without further purification

Sources & evidence

ORD record
ord-495f487bedfe4f41ae76334d5dcc0546
Source dataset
uspto-grants-2008_07
Patent number
US07393367B2

Reaction notes

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