Water → HCID 22999184, compound

HRID 1166767Notes

Reaction equation

HRID 1166767 reaction equation
[Br:1][CH2:2][CH2:3]Br.[Br:5][C:6]1[C:7]([OH:16])=[C:8]([O:14][CH3:15])[CH:9]=[C:10]([CH:13]=1)[CH:11]=[O:12].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[Br:1][CH2:2][CH2:3][O:16][C:7]1[C:8]([O:14][CH3:15])=[CH:9][C:10]([CH:11]=[O:12])=[CH:13][C:6]=1[Br:5]

Participants

6

Reactant 4

HCID 962WaterHCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 180995-Bromovanillin

Product 1

HCID 22999184HCID 22999184, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1,2-Dibromoethane (37 mL, 0.43 moles) was added to a mixture of 5-bromovanillin (10 g, 43 mmoles) and potassium carbonate (30 g, 216 mmoles) in DMF (150 ml) and the resulting mixture was stirred vigorously at room temperature for 16 hours followed by vigorously stirring at 60° C. for 16 hours. The cooled mixture was poured into water (1 L) and extracted with ethyl acetate (3×250 mL). The combined organic phases were washed with saturated sodium chloride (300 mL), dried over MgSO4 and evaporated in vacuo to afford 13.7 g (94%) of 4-(2-bromoethoxy)-3-bromo-5-methoxybenzaldehyde.

Workup

  1. stirringby vigorously stirring at 60° C. for 16 hours
  2. extractionextracted with ethyl acetate (3×250 mL)
  3. washThe combined organic phases were washed with saturated sodium chloride (300 mL)
  4. dry with materialdried over MgSO4
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-afdce1855ec447aaa7b1615b2709b653
Source dataset
uspto-grants-2003_09
Patent number
US06613942B1

Reaction notes

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