Hydrogen Bromide → HCID 22316212, compound

HRID 970261Notes

Reaction equation

HRID 970261 reaction equation
Cl[Si](C)(C)C.[Br:6][C:7]1[C:12]([CH3:13])=[CH:11][C:10]([CH3:14])=[CH:9][C:8]=1[CH3:15].[Mg].Br.[C:18]1([S:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=O)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1(C)C=CC=CC=1>[Br-:6].[C:26]1([S+:24]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:7]2[C:12]([CH3:13])=[CH:11][C:10]([CH3:14])=[CH:9][C:8]=2[CH3:15])[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

7

Reactant 5

HCID 260Hydrogen BromideHCID 6397ChlorotrimethylsilaneHCID 13679Diphenyl sulfoxideHCID 684732-BromomesityleneHCID 5462224Magnesium

Product 1

HCID 22316212HCID 22316212, compoundYield 48.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In 600 mL of tetrahydrofran, 24.0 g of diphenylsulfoxide was dissolved under nitrogen atmosphere, then the solution was charged with 31.5 g of chlorotrimethylsilane. To this solution, a Grignard reagent prepared with 60 g of 2-bromomesitylene and 4.70 g of magnesium according to the conventional method was added drop-wise with ice-cooling, followed by reacting at the same temperature for 3 hours. After completion of the reaction, 480 mL of a 24% aqueous hydrobromic acid solution and further 600 mL of toluene was poured drop-wise to said reaction solution and stirred. Then, the organic layer separated was extracted twice with 120 mL of a 12% aqueous hydrobromic acid solution and combined together with the water layer, which was further extracted three times with 480 mL of methylene chloride. The organic layer obtained was dried by anhydrous magnesium sulfate, followed by concentrating under reduced pressure, to obtain 22.0 g of diphenyl-2,4,6-trimethylphenylsulfonium bromide as a white crystal. The measurement results of melting point and NMR of the crystal obtained are shown bellow.

Workup

  1. additionwas added drop-wise with ice-
  2. temperaturecooling
  3. additionwas poured drop-wise
  4. customreaction solution
  5. customThen, the organic layer separated
  6. extractionwas extracted twice with 120 mL of a 12% aqueous hydrobromic acid solution
  7. extractionwas further extracted three times with 480 mL of methylene chloride
  8. customThe organic layer obtained
  9. dry with materialwas dried by anhydrous magnesium sulfate
  10. concentrationby concentrating under reduced pressure

Sources & evidence

ORD record
ord-f76dc3b07b854b9eae852b4757e0d8da
Source dataset
uspto-grants-2007_12
Patent number
US07312014B2

Reaction notes

Loading…