Allyl bromide → 3-Allyloxy-2,6-dichloro-benzaldehyde

HRID 450931Notes

Reaction equation

HRID 450931 reaction equation
[Cl:1][C:2]1[C:9]([OH:10])=[CH:8][CH:7]=[C:6]([Cl:11])[C:3]=1[CH:4]=[O:5].[CH2:12](Br)[CH:13]=[CH2:14].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:14]([O:10][C:9]1[C:2]([Cl:1])=[C:3]([C:6]([Cl:11])=[CH:7][CH:8]=1)[CH:4]=[O:5])[CH:13]=[CH2:12]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 104425302,6-Dichloro-3-hydroxy-benzaldehyde

Product 1

HCID 866124013-Allyloxy-2,6-dichloro-benzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,6-dichloro-3-hydroxybenzaldehyde (960 mg, 5.03 mmol) (Synthesis, 2004, 12, 2062), allyl bromide (431 μL, 5.03 mmol) and potassium carbonate (563 mg, 10.06 mmol) were combined in DMF (5 mL) and stirred at room temperature for 18 hours. The DMF was removed in vacuo and the residue partitioned between diethyl ether (50 mL) and water (30 mL). The layers were separated and the aqueous extracted with diethyl ether (2×30 mL). The combined organic solution was dried over magnesium sulphate and concentrated in vacuo to afford the title compound as a yellow solid which was used without further purification in preparation 75.

Workup

  1. customThe DMF was removed in vacuo
  2. customthe residue partitioned between diethyl ether (50 mL) and water (30 mL)
  3. customThe layers were separated
  4. extractionthe aqueous extracted with diethyl ether (2×30 mL)
  5. dry with materialThe combined organic solution was dried over magnesium sulphate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bb126bdaff1a41779905d16626e23b44
Source dataset
uspto-grants-2013_07
Patent number
US08486992B2

Reaction notes

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