Water → 4-(2-Bromoethoxy)-3-methoxybenzaldehyde

HRID 1166757Notes

Reaction equation

HRID 1166757 reaction equation
[Br:1][CH2:2][CH2:3]Br.[OH:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][C:7]=1[O:14][CH3:15].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[Br:1][CH2:2][CH2:3][O:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][C:7]=1[O:14][CH3:15]

Participants

6

Reactant 4

HCID 962WaterHCID 1183VanillinHCID 78391,2-DibromoethaneHCID 11430Potassium Carbonate

Product 1

HCID 160872944-(2-Bromoethoxy)-3-methoxybenzaldehydeYield 95.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1,2-Dibromoethane (57 mL, 0.66 moles) was added to a mixture of 4-hydroxy-3-methoxybenzaldehyde (10 g, 66 mmoles) and potassium carbonate (45 g, 0.33 moles) in DMF (130 ml) and the resulting mixture was stirred vigorously at room temperature for 16 hours. The mixture was poured into water (1.2 L) and extracted with ethyl acetate (500+4×300 mL). The combined organic phases were washed with saturated sodium chloride (500 mL), dried over MgSO4 and evaporated in vacuo to afford 16.3 g (95%) of 4-(2-bromoethoxy)-3-methoxybenzaldehyde. M.p. 61-64° C.

Workup

  1. extractionextracted with ethyl acetate (500+4×300 mL)
  2. washThe combined organic phases were washed with saturated sodium chloride (500 mL)
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-c68d14464df64a9e9538a06b9e73482f
Source dataset
uspto-grants-2003_09
Patent number
US06613942B1

Reaction notes

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