1-Bromopropane → 3-bromo-5-methoxy-4-propoxybenzaldehyde

HRID 728059Notes

Reaction equation

HRID 728059 reaction equation
[Br:1][C:2]1[C:3]([OH:12])=[C:4]([O:10][CH3:11])[CH:5]=[C:6]([CH:9]=1)[CH:7]=[O:8].C(=O)([O-])[O-].[K+].[K+].Br[CH2:20][CH2:21][CH3:22]>CN(C=O)C>[Br:1][C:2]1[CH:9]=[C:6]([CH:5]=[C:4]([O:10][CH3:11])[C:3]=1[O:12][CH2:20][CH2:21][CH3:22])[CH:7]=[O:8]

Participants

5

Reactant 3

HCID 78401-BromopropaneHCID 11430Potassium CarbonateHCID 180995-Bromovanillin

Product 1

HCID 20640193-bromo-5-methoxy-4-propoxybenzaldehydeYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

50 g (0.43 mole) of 5-bromovanillin in 130 ml of DMF was added 150 g (1.08 mole) of potassium carbonate and 55 ml (0.606 mole) of bromopropane. The mixture was stirred for 72 hours at 70° C. The solution was then poured into 1 liter ice water. The aqueous solution was extracted with 3×200 ml CH2Cl2, the combined organic extracts were dried over MgSO4. The solution was filtered and the filtrate was concentrated to dryness to yield 66.80 g of 3-bromo-5-methoxy-4-propoxybenzaldehyde as a yellow oil. (95% yield).

Workup

  1. extractionThe aqueous solution was extracted with 3×200 ml CH2Cl2
  2. dry with materialthe combined organic extracts were dried over MgSO4
  3. filtrationThe solution was filtered
  4. concentrationthe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-a915c6b48a92425194dfce06e1e3dbd3
Source dataset
uspto-grants-1991_09
Patent number
US05047420

Reaction notes

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