Water → HCID 22999110, compound

HRID 1166758Notes

Reaction equation

HRID 1166758 reaction equation
[Br:1][CH2:2][CH2:3]Br.[Cl:5][C:6]1[CH:7]=[C:8]([CH:11]=[C:12]([O:15][CH3:16])[C:13]=1[OH:14])[CH:9]=[O:10].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[Br:1][CH2:2][CH2:3][O:14][C:13]1[C:12]([O:15][CH3:16])=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][C:6]=1[Cl:5]

Participants

6

Reactant 4

HCID 962WaterHCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 296223-Chloro-4-hydroxy-5-methoxybenzaldehyde

Product 1

HCID 22999110HCID 22999110, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1,2-Dibromoethane (46 mL, 0.54 moles) was added to a mixture of 3-chloro-4-hydroxy-5-methoxybenzaldehyde (10 g, 54 mmoles) and potassium carbonate (37 g, 0.27 moles) in DMF (180 ml) and the resulting mixture was stirred vigorously at room temperature for 16 hours. The mixture was poured into water (100 mL) and extracted with ethyl acetate (2×100 mL). The combined organic phases were washed with saturated sodium chloride (150 mL), dried over MgSO4 and evaporated in vacuo to afford 9.33 g (59%) of 4-(2-bromoethoxy)-3-chloro-5-methoxybenzaldehyde. M.p. 52-54° C.

Workup

  1. extractionextracted with ethyl acetate (2×100 mL)
  2. washThe combined organic phases were washed with saturated sodium chloride (150 mL)
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-c3892c23f84744dd824157adb5ab805f
Source dataset
uspto-grants-2003_09
Patent number
US06613942B1

Reaction notes

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