Isopropyl iodide → 5-Bromo-2-isopropoxybenzaldehyde

HRID 1290009Notes

Reaction equation

HRID 1290009 reaction equation
[Br: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+].I[CH:18]([CH3:20])[CH3:19]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH:18]([CH3:20])[CH3:19])=[C:6]([CH:9]=1)[CH:7]=[O:8]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 728635-Bromosalicylaldehyde

Product 1

HCID 8199735-Bromo-2-isopropoxybenzaldehydeYield 98.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-bromosalicylaldehyde (5.0 gm, 0.025 mol) in DMF (40 mL) were added powdered potassium carbonate (5.15 gm, 0.037 mol) and 2-iodopropane (3.5 mL, 0.035 mol) dropwise with stirring. The mixture was stirred overnight at room temperature, partitioned between diethyl ether and water. The aqueous was extracted with ether, and the combined organic layers were washed with water, saturated brine solution, dried (Na2 SO4), and evaporated to afford 6.0 gm of pure title compound.

Workup

  1. stirringThe mixture was stirred overnight at room temperature
  2. custompartitioned between diethyl ether and water
  3. extractionThe aqueous was extracted with ether
  4. washthe combined organic layers were washed with water, saturated brine solution
  5. customdried (Na2 SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-e694d8303e3c4e2cb18cd3636ecb6414
Source dataset
uspto-grants-1998_05
Patent number
US05750549

Reaction notes

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