4-Hydroxybenzaldehyde → 4-(2-Bromoethoxy)Benzaldehyde

HRID 1400672Notes

Reaction equation

HRID 1400672 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][CH:7]=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O.C(OCC)(=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][CH:7]=1

Participants

6

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 78391,2-DibromoethaneHCID 11430Potassium Carbonate

Product 1

HCID 2627064-(2-Bromoethoxy)BenzaldehydeYield 44%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1,2-dibromoethane (3.9 mL, 45 mmol), 4-hydroxybenzaldehyde (1.8 g, 15 mmol) and K2CO3 (10.4 g, 75 mmol) in acetone (40 mLO was heated to reflux for 18 hr. The mixture was cooled, diluted with ethyl acetate (200 mL) and washed with brine (200 mL). Then organic layer was dried (MgSO4), filtered and then concentrated. The resulting residue was subjected to flash chromatography (25% ethyl acetate/hexane) to provide 1.51 g (44%) of 4-(2-bromoethoxy)benzaldehyde.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 18 hr
  3. temperatureThe mixture was cooled
  4. washwashed with brine (200 mL)
  5. dry with materialThen organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-72ef8fe73634470683beafe005ee4995
Source dataset
uspto-grants-2014_12
Patent number
US08906954B2

Reaction notes

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