Allyl bromide → Benzaldehyde, 3-iodo-5-methoxy-4-(2-propenyloxy)-

HRID 1085625Notes

Reaction equation

HRID 1085625 reaction equation
[CH2:1](Br)[CH:2]=[CH2:3].[I:5][C:6]1[C:7]([OH:16])=[C:8]([O:14][CH3:15])[CH:9]=[C:10]([CH:13]=1)[CH:11]=[O:12].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:1]([O:16][C:7]1[C:6]([I:5])=[CH:13][C:10]([CH:11]=[O:12])=[CH:9][C:8]=1[O:14][CH3:15])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 79499Benzaldehyde, 4-hydroxy-3-iodo-5-methoxy-

Product 1

HCID 4382547Benzaldehyde, 3-iodo-5-methoxy-4-(2-propenyloxy)-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Allyl bromide (27.5 ml, 0.32 mol) was added to a solution of 5-iodovanillin (50.0 g, 0.18 mol) in DMF (200 ml) containing potassium carbonate (48 g, 0.35 mol) at 80° C. The mixture was stirred at this temperature for 1 hour, filtered, and the filtrate was evaporated to a residue, which was purified by HPLC (hexane-ethyl acetate, 4:1, v/v) to give 4-allyloxy-5-iodo-3-methoxybenzaldehyde.

Workup

  1. filtrationfiltered
  2. customthe filtrate was evaporated to a residue, which
  3. customwas purified by HPLC (hexane-ethyl acetate, 4:1

Sources & evidence

ORD record
ord-09b2db7817de4c739fa1efd09c4a4ec5
Source dataset
uspto-grants-1991_04
Patent number
US05010100

Reaction notes

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