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

HRID 1166756Notes

Reaction equation

HRID 1166756 reaction equation
[Br:1][CH2:2][CH2:3]Br.[OH:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[C:8]([O:14][CH3:15])[CH:7]=1.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])=[C:8]([O:14][CH3:15])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 5195414-Hydroxy-2-Methoxybenzaldehyde

Product 1

HCID 229991114-(2-Bromoethoxy)-2-methoxybenzaldehydeYield 101.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1,2-Dibromoethane (57 mL, 0.66 moles) was added to a mixture of 4-hydroxy-2-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 (0.8 L) and extracted with ethyl acetate (3×300 mL). The combined organic phases were washed with saturated sodium chloride (400 mL), dried over MgSO4 and evaporated in vacuo to afford 17.4 g (99%) of 4-(2-bromoethoxy)-2-methoxybenzaldehyde, M.p. 78-79° C.

Workup

  1. extractionextracted with ethyl acetate (3×300 mL)
  2. washThe combined organic phases were washed with saturated sodium chloride (400 mL)
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-134a61f2fe4148b980a2502d8c85f205
Source dataset
uspto-grants-2003_09
Patent number
US06613942B1

Reaction notes

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