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

HRID 2387671Notes

Reaction equation

HRID 2387671 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-aecdb0f79b534af9859f1b284317aaa7
Source dataset
uspto-grants-2012_09
Patent number
US08268881B2

Reaction notes

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