Iodoethane → 2-Bromo-5-ethoxybenzaldehyde

HRID 402762Notes

Reaction equation

HRID 402762 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:3]=1[CH:4]=[O:5].I[CH2:12][CH3:13].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[Br:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH2:12][CH3:13])=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 3871792-Bromo-5-hydroxybenzaldehyde

Product 1

HCID 30164192-Bromo-5-ethoxybenzaldehydeYield 80.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-bromo-5-hydroxybenzaldehyde (5 g, 24.87 mmol) in DMF (20 mL) was added iodoethane (5.82 g, 37.3 mmol) and K2CO3 (6.88 g, 49.7 mmol) portion wise. The resulting reaction mixture was stirred at 50° C. overnight. After cooling, the mixture was diluted with EtOAc/hexanes (1:1) and water. Layers were separated and the organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated to give the title intermediate (4.6 g) as white solid.

Workup

  1. customThe resulting reaction mixture
  2. temperatureAfter cooling
  3. customLayers were separated
  4. washthe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-afb8f9bb4f244c02a5f08709b0479674
Source dataset
uspto-grants-2014_06
Patent number
US08742110B2

Reaction notes

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