Water → HCID 2213786, compound

HRID 1174058Notes

Reaction equation

HRID 1174058 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([I:10])=[CH:6][C:3]=1[CH:4]=[O:5].C([O-])([O-])=O.[K+].[K+].[CH2:17](Br)[CH:18]=[CH2:19].O>CN(C)C=O>[CH2:19]([O:1][C:2]1[CH:9]=[CH:8][C:7]([I:10])=[CH:6][C:3]=1[CH:4]=[O:5])[CH:18]=[CH2:17]

Participants

6

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 2526125-Iodosalicylaldehyde

Product 1

HCID 2213786HCID 2213786, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2-hydroxy-5-iodo-benzaldehyde (16 g, 64.5 mmol) (Aldrich) in N,N-dimethylformamide (100 mL) was added K2CO3 (16 g, 115 mmo) and allyl bromide (20 g, 165 mmol) (Aldrich). The reaction mixture was stirred at 100° C. for 3 h, then cooled to room temperature and poured into water, extracted with ethyl acetate. The organic layers were combined, washed with water, brine, dried over MgSO4, filtered and concentrated to give 2-allyloxy-5-iodo-benzaldehyde as a white solid (Yield: 18g, 97%).

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washwashed with water, brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e1af5bdaab184b2e8d0fbeeb4c543f80
Source dataset
uspto-grants-2010_11
Patent number
US07834179B2

Reaction notes

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