Water → HCID 86612271, compound

HRID 2355208Notes

Reaction equation

HRID 2355208 reaction equation
[Br:1][C:2]1[CH:9]=[C:8](F)[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[C:11]1([S:17]([O-:19])=[O:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[Na+].O>CS(C)=O>[C:11]1([S:17]([C:8]2[CH:7]=[CH:6][C:3]([CH:4]=[O:5])=[C:2]([Br:1])[CH:9]=2)(=[O:19])=[O:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2723840Benzenesulfinic acid, sodium saltHCID 27733192-Bromo-4-fluorobenzaldehyde

Product 1

HCID 86612271HCID 86612271, compoundYield 32.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of 2-bromo-4-fluorobenzaldehyde (10.2 g, 50 mmol) and sodium benzenesulfinate (8.21 g, 50 mmol) in DMSO (100 mL) was heated at 125° C. overnight. Upon cooling the mixture was poured into water and extracted with EtOAc. The combined organic extracts were washed with water and brine, dried over Na2SO4, filtered and evaporated in vacuo. The residue was purified via flash chromatography (hexane/EtOAc, 4/1) to give 4-benzenesulfonyl-2-bromo-benzaldehyde (5.26 g, 32% yield) as white crystalline solid.

Workup

  1. temperatureUpon cooling the mixture
  2. extractionextracted with EtOAc
  3. washThe combined organic extracts were washed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue was purified via flash chromatography (hexane/EtOAc, 4/1)

Sources & evidence

ORD record
ord-dfa079e1f4474c31850b25913ca99403
Source dataset
uspto-grants-2010_07
Patent number
US07754759B2

Reaction notes

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