Phenacyl bromide → HCID 19354077, compound

HRID 378491Notes

Reaction equation

HRID 378491 reaction equation
[CH2:1](Br)[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:3].[F:11][Sb-:12]([F:17])([F:16])([F:15])([F:14])[F:13].[Na+].[CH2:19]([S:37][CH3:38])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36].[Br-].[Na+]>C(C(C)=O)C>[F:11][Sb-:12]([F:17])([F:16])([F:15])([F:14])[F:13].[CH3:38][S+:37]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH2:1][C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:3]

Participants

6

Reactant 4

HCID 6259Phenacyl bromideHCID 253881Sodium BromideHCID 536381methyloctadecylsulfideHCID 16689647Sodium hexafluoroantimonate

Product 1

HCID 19354077HCID 19354077, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

In a 100 mL Erlenmeyer flask were combined 10 g (0.05 mol) phenacyl bromide, 12.93 g (0.05 mol) sodium hexafluoroantimonate, 15 g (0.05 mol) methyl octadecyl sulfide and 40 mL methyl ethyl ketone (2-butanone). The reaction mixture was heated to boiling and maintained at this temperature for 30 minutes. During this time, sodium bromide was observed to precipitate. The reaction mixture was filtered to remove the inorganic salts and the resulting solution placed on a rotary evaporator to remove solvents. The product crystallized to give the desired salt, m.p. 80-82° C. Recrystallization from isopropanol gave a very light tan salt with a melting point of 79-80° C.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperaturemaintained at this temperature for 30 minutes
  3. customto precipitate
  4. filtrationThe reaction mixture was filtered
  5. customto remove the inorganic salts
  6. customthe resulting solution placed on a rotary evaporator
  7. customto remove solvents
  8. customThe product crystallized

Sources & evidence

ORD record
ord-4e7a78235a094b98b9fdb25f1cc51634
Source dataset
uspto-grants-2000_02
Patent number
US06031014

Reaction notes

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