Potassium Iodide → 2-(Benzyloxy)-5-bromobenzaldehyde

HRID 1686139Notes

Reaction equation

HRID 1686139 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.C(OCC)(=O)C>[CH2:11]([O:10][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:9][C:6]=1[CH:7]=[O:8])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 728635-Bromosalicylaldehyde

Product 1

HCID 7330872-(Benzyloxy)-5-bromobenzaldehydeYield 81.1%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-bromo-2-hydroxybenzaldehyde (5 g, 24.9 mmol) in acetone (200 mL) were added benzyl bromide (5.11 mL, 29.9 mmol), potassium iodide (KI, 2.07 g, 12.45 mmol) and potassium carbonate (K2CO3, 5.17 g, 37.4 mmol), followed by mixing at 70° C. for 2 hours under a reflux condition. The product thus obtained was diluted in ethyl acetate (EtOAc), washed with brine, and dried over magnesium sulfate (MgSO4) to concentrate it. The concentrate was purified using silica column chromatography (10% ethyl acetate/hexane) to afford the title compound (5.88 g, 81%).

Workup

  1. additionby mixing at 70° C. for 2 hours under a reflux condition
  2. customThe product thus obtained
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate (MgSO4)
  5. concentrationto concentrate it
  6. customThe concentrate was purified

Sources & evidence

ORD record
ord-ba669eb5331e4c4fb02aab976f41d55b
Source dataset
uspto-grants-2012_04
Patent number
US08148541B2

Reaction notes

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