Hydrogen Bromide → HCID 85829357, compound

HRID 2212626Notes

Reaction equation

HRID 2212626 reaction equation
[C:1]1([S:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:15]1([S:21]C2C=CC=CC=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Br-:28].[Al+3].[Br-].[Br-].Br>CCCCCC.CC(C)=O>[Br-:28].[C:1]1([S+:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:9]2[CH:14]=[CH:13][C:12]([S:21][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 260Hydrogen BromideHCID 8766Diphenyl sulfideHCID 13679Diphenyl sulfoxideHCID 166749Bromhydrol

Product 1

HCID 85829357HCID 85829357, compoundYield 78.3%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8058HexaneSolvent

Conditions

Temperature
5 °C

Procedure

In 200 ml of n-hexane were suspended 6.07 g (0.03 mol) of diphenylsulfoxide and 11.2 g (0.06 mol) of diphenylsulfide, and 48.0 g (0.18 mol) of aluminum bromide was added thereto at 20 to 40° C., followed by reacting at 60 to 65° C. for 6 hours with stirring. After completion of the reaction, the reaction solution was poured into 500 ml of 12% hydrobromic acid, followed by washing with 200 ml of n-hexane five times and extracting with 200 ml of dichloromethane. The obtained dichloromethane layer was washed with 200 ml of water five times, followed by concentration under reduced pressure to obtain a crude product. Then, 120 ml of acetone was added to the crude product to dissolve at 55° C., followed by cooling to 5° C. to obtain crystal. The crystal was filtered off to obtain 5.3 g (Yield: 39%) of dipheny-4-phenylthiophenylsulfonium bromide as a pale yellow crystal.

Workup

  1. additionwas added
  2. customat 20 to 40° C.
  3. customAfter completion of the reaction
  4. washby washing with 200 ml of n-hexane five times
  5. extractionextracting with 200 ml of dichloromethane
  6. washThe obtained dichloromethane layer was washed with 200 ml of water five times
  7. concentrationfollowed by concentration under reduced pressure
  8. customto obtain a crude product
  9. dissolutionto dissolve at 55° C.
  10. customto obtain crystal
  11. filtrationThe crystal was filtered off

Sources & evidence

ORD record
ord-c96cb19eefb54cdd967fcb4c0a1f4db7
Source dataset
uspto-grants-2006_09
Patent number
US07101918B2

Reaction notes

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