Water → 4-Bromo-1,2-diethoxybenzene

HRID 1978614

Reaction equation

HRID 1978614 reaction equation
[Br:1][C:2]1[CH:3]=[C:4](O)[C:5](=[CH:7][CH:8]=1)[OH:6].[C:10](=[O:13])([O-])[O-].[K+].[K+].[CH2:16](I)[CH3:17].O.[CH3:20]N(C=O)C>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:16][CH3:17])=[C:7]([O:13][CH2:10][CH3:20])[CH:8]=1

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 284874-Bromocatechol

Product 1

HCID 130876394-Bromo-1,2-diethoxybenzene

Procedure

To a mixture of 4-bromocathechol (8.43 g) and potassium carbonate (15.4 g) in DMF (80 ml) was added at room temperature ethyl iodide (7.5 ml), and the mixture was stirred for 15 hours. To the mixture was added water, and the mixture was extracted with hexane. The organic layer was washed with water and saturated brine, dried with magnesium sulfate and concentrated under reduced pressure, and the residue purified with silica gel column chromatography (ethyl acetate/hexane=1:4) to give yellow oil of 4-bromo-1,2-diethoxybenzene (10.06 g).

Workup

  1. extractionthe mixture was extracted with hexane
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried with magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customthe residue purified with silica gel column chromatography (ethyl acetate/hexane=1:4)

Sources & evidence

ORD record
ord-0df10e4800184c89a7c6de88cd66c5f0
Source dataset
uspto-grants-2001_05
Patent number
US06235771B1

Linked notes

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