Allyl bromide → 5-Chloro-2-[(prop-2-en-1-yl)oxy]benzaldehyde

HRID 2036225Notes

Reaction equation

HRID 2036225 reaction equation
[Cl:1][C:2]1[CH:9]=[C:6]([CH:7]=[O:8])[C:5]([OH:10])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:17](Br)[CH:18]=[CH2:19]>CN(C=O)C.O>[CH2:19]([O:10][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:9][C:6]=1[CH:7]=[O:8])[CH:18]=[CH2:17]

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 124815-Chloro-salicylaldehyde

Product 1

HCID 44703325-Chloro-2-[(prop-2-en-1-yl)oxy]benzaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of 5-chlorosalicylaldehyde (8.20 g, 52.37 mmol, 1.00 eq.) and potassium carbonate anhydrous (8.69 g, 62.85 mmol, 1.20 eq.) in DMF (100 mL), allyl bromide (4.7 mL, 54.99 mmol, 1.05 eq.) was added. The mixture was heated at 50° C. for 18 hours. The reaction mixture was allowed to cool to r.t. and poured in water (150 mL). The mixture was extracted with DCM (2×200 mL). The comb. org. phases were dried over MgSO4 and concentrated in vacuo to give 2-allyloxy-5-chloro-benzaldehyde. The product was used without further purification.

Workup

  1. additionwas added
  2. temperatureto cool to r.t.
  3. extractionThe mixture was extracted with DCM (2×200 mL)
  4. dry with materialphases were dried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0a010494a46f49718df8476b1bd9229a
Source dataset
uspto-grants-2013_11
Patent number
US08575158B2

Reaction notes

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