Hydrochloric Acid → Triphenylsulfonium 1,1-difluoro-2-(4-vinyl-benzoyloxy)-ethane-1-sulfonate

HRID 424335

Reaction equation

HRID 424335 reaction equation
[CH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1)=[CH2:2].[F:12][C:13]([F:20])([S:16]([O-:19])(=[O:18])=[O:17])[CH2:14][OH:15].[C:21]1([S+:27]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(N(CC)CC)C.Cl>C(Cl)Cl>[F:12][C:13]([F:20])([S:16]([O-:19])(=[O:18])=[O:17])[CH2:14][O:15][C:7](=[O:8])[C:6]1[CH:10]=[CH:11][C:3]([CH:1]=[CH2:2])=[CH:4][CH:5]=1.[C:34]1([S+:27]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 110520284-Vinylbenzoyl chlorideHCID 86632756HCID 86632756, compound

Product 1

HCID 86640944Triphenylsulfonium 1,1-difluoro-2-(4-vinyl-benzoyloxy)-ethane-1-sulfonateYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Under ice cooling, 2.0 g (12 mmol) of the 4-vinylbenzoyl chloride in methylene chloride was added dropwise to a mixture of 4.2 g (10 mmol) of triphenylsulfonium 1,1-difluoro-2-hydroxyethanesulfonate in Synthesis Example 1-13, 1.21 g (12 mmol) of triethylamine, 0.24 g (2 mmol) of N,N-dimethylaminopyridine, and 20 g of methylene chloride. The resulting mixture was stirred for 2 hours at room temperature. Thereafter, 11 g of 5% dilute hydrochloric acid was added to the reaction mixture. The organic layer was taken out and washed with water, from which methylene chloride was distilled off in vacuum. 30 g of methyl isobutyl ketone was added to the residue, which was washed with dilute aqueous ammonia and then with water. Thereafter, methyl isobutyl ketone was distilled off in vacuum. Diisopropyl ether was added to the residue. By decantation, the target compound, triphenylsulfonium 1,1-difluoro-2-(4-vinyl-benzoyloxy)-ethane-1-sulfonate was obtained. Colorless oil, 5.1 g (yield 86%). The compound has the following structure.

Workup

  1. washwashed with water, from which methylene chloride
  2. distillationwas distilled off in vacuum
  3. addition30 g of methyl isobutyl ketone was added to the residue, which
  4. washwas washed with dilute aqueous ammonia
  5. distillationThereafter, methyl isobutyl ketone was distilled off in vacuum
  6. additionDiisopropyl ether was added to the residue

Sources & evidence

ORD record
ord-80296f7614b5459da4bb30f95234190a
Source dataset
uspto-grants-2012_01
Patent number
US08105748B2

Linked notes

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