Ethanol → 4-Bromo-2-(diethoxymethyl)-1-iodobenzene

HRID 1189978Notes

Reaction equation

HRID 1189978 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([I:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].[CH3:11][C:12]1C=CC(S(O)(=O)=O)=CC=1.[CH2:22]([OH:24])[CH3:23]>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([I:10])=[C:6]([CH:7]([O:24][CH2:22][CH3:23])[O:8][CH2:11][CH3:12])[CH:9]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 6101p-Toluenesulfonic acidHCID 219738615-Bromo-2-iodobenzaldehyde

Product 1

HCID 672964774-Bromo-2-(diethoxymethyl)-1-iodobenzene

Procedure

A mixture of 5-bromo-2-iodobenzaldehyde (14.9) (1.0 g, 3.2 mmol) and PTSA (0.1 g) in ethanol was stirred under reflux for 18 hrs and concentrated under reduced pressure. The residue was dissolved in ethyl acetate and washed with saturated NaHCO3, dried over anhydrous Na2SO4 and concentrated to give 4-bromo-2-(diethoxymethyl)-1-iodobenzene (14.10) that was directly used in next reaction without further purification.

Workup

  1. temperatureunder reflux for 18 hrs
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with saturated NaHCO3
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7fec32c7e7854cfea01b2c14f6c21bf9
Source dataset
uspto-grants-2014_03
Patent number
US08674137B2

Reaction notes

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