Hydrochloric Acid → 4-Fluorophenyldiphenylsulfonium chloride

HRID 1920612Notes

Reaction equation

HRID 1920612 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[Si]([Cl:19])(C)C.[Mg].[F:21][C:22]1[CH:27]=[CH:26][C:25](Cl)=[CH:24][CH:23]=1.Cl>ClCCl.C(OCC)C.O.O1CCCC1>[Cl-:19].[F:21][C:22]1[CH:27]=[CH:26][C:25]([S+:7]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:24][CH:23]=1

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 6397ChlorotrimethylsilaneHCID 9604Benzene, 1-chloro-4-fluoro-HCID 13679Diphenyl sulfoxideHCID 5462224Magnesium

Product 1

HCID 866496604-Fluorophenyldiphenylsulfonium chloride

Reagents, catalysts & solvents 4

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Diphenyl sulfoxide, 40 g (0.2 mole), was dissolved in 400 g of dichloromethane, which was stirred under ice cooling. At a temperature below 20° C., 65 g (0.6 mole) of trimethylsilyl chloride was added dropwise to the solution, which was allowed to mature for 30 minutes at the temperature. Then, a Grignard reagent which had been prepared from 14.6 g (0.6 mole) of metallic magnesium, 78.3 g (0.6 mole) of 4-fluorochlorobenzene and 180 g of tetrahydrofuran (THF) was added dropwise at a temperature below 20° C. The reaction solution was allowed to mature for one hour, after which 50 g of water at a temperature below 20° C. was added to quench the reaction. To this solution, 150 g of water, 10 g of 12N hydrochloric acid, and 200 g of diethyl ether were further added. The water layer was separated and washed with 100 g of diethyl ether, yielding an aqueous solution of 4-fluorophenyldiphenylsulfonium chloride. The compound in aqueous solution form was used in the subsequent reaction without further isolation.

Workup

  1. additionwas added dropwise at a temperature below 20° C
  2. waitto mature for one hour
  3. customto quench
  4. customthe reaction
  5. customThe water layer was separated
  6. washwashed with 100 g of diethyl ether

Sources & evidence

ORD record
ord-9e58f05476904428a99705af8f21d670
Source dataset
uspto-grants-2012_05
Patent number
US08173354B2

Reaction notes

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