Phenyltrimethylammonium bromide dibromide → HCID 58136833, compound

HRID 1258522Notes

Reaction equation

HRID 1258522 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:16](=[O:18])[CH3:17])[CH:7]=[C:8]([S:10]([F:15])([F:14])([F:13])([F:12])[F:11])[CH:9]=1)[CH3:2].[Br-:19].[Br-].[Br-].C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1>C1COCC1.C(Cl)Cl>[Br:19][CH2:17][C:16]([C:6]1[CH:7]=[C:8]([S:10]([F:11])([F:12])([F:13])([F:15])[F:14])[CH:9]=[C:4]([O:3][CH2:1][CH3:2])[CH:5]=1)=[O:18]

Participants

5

Reactant 2

HCID 17977687Phenyltrimethylammonium bromide dibromideHCID 58136890HCID 58136890, compound

Product 1

HCID 58136833HCID 58136833, compoundYield 125.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-[3-Ethoxy-5-(pentafluorosulfanyl)phenyl]ethanone (2.07 g) was dissolved in THF (80 ml) and phenyltrimethylammonium tribromide (2.90 g) was added while stirring. After stirring at RT for 3 h, the mixture was diluted with DCM and washed once with 5% sodium thiosulfate solution. The DCM phase was dried over magnesium sulfate, filtered and concentrated. The residue was purified using silica gel (120 g cartridge, n-heptane/MtB ether gradient of 0-20% within 60 min). 2.07 g of the title compound were obtained.

Workup

  1. stirringAfter stirring at RT for 3 h
  2. washwashed once with 5% sodium thiosulfate solution
  3. dry with materialThe DCM phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified
  7. customsilica gel (120 g cartridge, n-heptane/MtB ether gradient of 0-20% within 60 min)

Sources & evidence

ORD record
ord-fc15616d8e5548819b609d3396bee2fd
Source dataset
uspto-grants-2013_06
Patent number
US08466169B2

Reaction notes

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