Hydrochloric Acid → Bis[4-(tert-butyl)phenyl](4-fluorophenyl)sulfonium bromide

HRID 1753668Notes

Reaction equation

HRID 1753668 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][CH:3]=1.[C:9]([C:13]1[CH:18]=[CH:17][C:16]([S:19]([C:21]2[CH:26]=[CH:25][C:24]([C:27]([CH3:30])([CH3:29])[CH3:28])=[CH:23][CH:22]=2)=O)=[CH:15][CH:14]=1)([CH3:12])([CH3:11])[CH3:10].C[Si](Cl)(C)C.Cl>C(Cl)Cl>[Br-:1].[C:27]([C:24]1[CH:25]=[CH:26][C:21]([S+:19]([C:16]2[CH:15]=[CH:14][C:13]([C:9]([CH3:12])([CH3:11])[CH3:10])=[CH:18][CH:17]=2)[C:2]2[CH:7]=[CH:6][C:5]([F:8])=[CH:4][CH:3]=2)=[CH:22][CH:23]=1)([CH3:30])([CH3:29])[CH3:28]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6397ChlorotrimethylsilaneHCID 99931-Bromo-4-fluorobenzeneHCID 184321184,4'-Sulfinylbis(tert-butylbenzene)

Product 1

HCID 131733658Bis[4-(tert-butyl)phenyl](4-fluorophenyl)sulfonium bromideYield 96.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a Grignard reagent prepared from 79 g of 1-bromo-4-fluorobenzene, 47 g of bis(4-tert-butylphenyl) sulfoxide obtained in Synthesis Example 1-2 and 150 g of methylene chloride were added. Under ice cooling, 49 g of trimethylsilyl chloride was added dropwise. The reaction solution was aged for 30 minutes, after which 105 g of 5 wt % dilute hydrochloric acid was added dropwise to quench the reaction. The organic layer was separated and concentrated in vacuum. Diisopropyl ether was added to the concentrate for recrystallization. The resulting crystals were collected by filtration and dried in vacuum, obtaining 68 g of the target compound, bis(4-tert-butylphenyl)(4-fluorophenyl)sulfonium bromide as white crystals. Yield 96%.

Workup

  1. additionwere added
  2. customto quench
  3. customthe reaction
  4. customThe organic layer was separated
  5. concentrationconcentrated in vacuum
  6. additionDiisopropyl ether was added to the
  7. concentrationconcentrate for recrystallization
  8. filtrationThe resulting crystals were collected by filtration
  9. customdried in vacuum

Sources & evidence

ORD record
ord-dcc9fcd8002c4dda9d09c8a8d3bef71a
Source dataset
uspto-grants-2015_10
Patent number
US09164384B2

Reaction notes

Loading…