Phenacyl bromide → HCID 16688854, compound

HRID 378492Notes

Reaction equation

HRID 378492 reaction equation
[CH2:1]([S:9][CH3:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH2:11](Br)[C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:13].[F:21][Sb-:22]([F:27])([F:26])([F:25])([F:24])[F:23].[Na+]>CC(C)=O>[F:21][Sb-:22]([F:27])([F:26])([F:25])([F:24])[F:23].[CH3:10][S+:9]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[CH2:11][C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:13]

Participants

5

Reactant 3

HCID 6259Phenacyl bromideHCID 77289Methyl octyl sulfideHCID 16689647Sodium hexafluoroantimonate

Product 1

HCID 16688854HCID 16688854, compoundYield 83.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Into a 100 mL round bottom flask equipped with a magnetic stirrer and reflux condenser were placed 16.0 g (0.1 mol) methyl octyl sulfide (obtained from the Aldrich Chemical Co.), 19.9 g (0.1 mol) phenacyl bromide, 25.87 g (0.1 mol) sodium hexafluoroantimonate and 40 mL acetone. The reaction mixture was brought to reflux and held at this temperature for 15 minutes. The mixture was filtered through a plug of glass wool (to remove the sodium bromide which was formed during the reaction) and the solvent was removed on a rotary evaporator, leaving 43.1 g (83.6% yield) of the desired methyl octylphenacylsulfonium hexafluoroantimonate as a tan colored solid. The product was further purified by recrystallization, first from a 1:3 mixture of water and ethanol, then, isopropanol. The pure, colorless, crystalline initiator had a melting point of 75-76° C. The initiator was soluble in a wide variety of common solvents such as acetone, methyl ethyl ketone, chloroform and methylene chloride.

Workup

  1. customInto a 100 mL round bottom flask equipped with a magnetic stirrer
  2. temperaturereflux condenser
  3. customobtained from the Aldrich Chemical Co
  4. temperatureto reflux
  5. filtrationThe mixture was filtered through a plug of glass wool (
  6. customto remove the sodium bromide which
  7. customwas formed during the reaction) and the solvent
  8. customwas removed on a rotary evaporator

Sources & evidence

ORD record
ord-375022e9429445c7b876d2db2d6dc90f
Source dataset
uspto-grants-2000_02
Patent number
US06031014

Reaction notes

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