Pyridine → Bromomethyl phenyl sulfoxide

HRID 926964Notes

Reaction equation

HRID 926964 reaction equation
[C:1]1([S:7]([CH3:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.[Br:16]Br>C(#N)C>[C:1]1([S:7]([CH2:9][Br:16])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 14516Methyl phenyl sulfoxideHCID 24408Bromine

Product 1

HCID 11816834Bromomethyl phenyl sulfoxide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
-40 °C

Procedure

Methyl phenyl sulfoxide (21.644 g, 154.4 mmol) was dissolved in anhydrous pyridine (27.4 mL, 2.2 eq) and dry acetonitrile (100 mL). The solution was cooled to −40° C. under an argon atmosphere. A solution of bromine (49.4 g, 2 eq) in dry acetonitrile (50 mL) was added slowly, maintaining the same temperature. The mixture was stirred at −40° C. for 1 h and then overnight at room temperature. The solvent was evaporated under vacuum and the residue was dissolved in dichloromethane. The organic layer was washed with Na2S2O3 20%, dried over anhydrous Na2SO4 and concentrated to dryness.

Workup

  1. temperaturemaintaining the same temperature
  2. customovernight
  3. customat room temperature
  4. customThe solvent was evaporated under vacuum
  5. dissolutionthe residue was dissolved in dichloromethane
  6. washThe organic layer was washed with Na2S2O3 20%
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-6699554b2ec94768832262f9bdd025a6
Source dataset
uspto-grants-2016_03
Patent number
US09290446B2

Reaction notes

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