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Hydrochloric Acid → Triphenylsulfonium 2-(4-chlorobutyryloxy)-1,1,3,3,3-pentafluoropropane-1-sulfonate

HRID 556243
Notes
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Reaction equation

HRID 556243 reaction equation
[OH:1][CH:2]([C:10]([F:13])([F:12])[F:11])[C:3]([F:9])([F:8])[S:4]([O-:7])(=[O:6])=[O:5].[C:14]1([S+:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.Cl[CH:34]([CH2:38][CH3:39])[C:35](Cl)=[O:36].N1C=CC=CC=1.[ClH:46]>C(#N)C>[Cl:46][CH2:39][CH2:38][CH2:34][C:35]([O:1][CH:2]([C:10]([F:13])([F:11])[F:12])[C:3]([F:8])([F:9])[S:4]([O-:7])(=[O:6])=[O:5])=[O:36].[C:27]1([S+:20]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 1390532-Chlorobutanoyl chlorideHCID 86612198Triphenylsulfonium 2-hydroxy-1,1,3,3,3-pentafluoropropanesulfonate

Product 1

HCID 86639509Triphenylsulfonium 2-(4-chlorobutyryloxy)-1,1,3,3,3-pentafluoropropane-1-sulfonateYield 88.7%

Reagents, catalysts & solvents

1
HCID 6342AcetonitrileSolvent2×

Procedure

To a mixture of 7.39 g (0.015 mole) of triphenylsulfonium 2-hydroxy-1,1,3,3,3-pentafluoropropane-1-sulfonate, 2.33 g (0.017 mole) of chlorobutyric chloride, and 37 g of acetonitrile, 1.42 g (0.018 mole) of pyridine was added dropwise, followed by stirring at room temperature for 3 hours. Then 18 g of 5% dilute hydrochloric acid was added to the reaction solution whereupon acetonitrile was distilled off under vacuum. The residue was combined with 40 g of dichloromethane whereupon the organic layer was separated. The organic layer was washed with 30 g of water, from which dichloromethane was distilled off under vacuum. To the residue was added 40 g of methyl isobutyl ketone. This was washed with 30 g of water, with 30 g of dilute aqueous ammonia, and three times with 30 g of water whereupon methyl isobutyl ketone was distilled off under vacuum. Ether was added to the residue, followed by decantation and vacuum drying. The target compound was obtained as brown oil (7.94 g, yield 87%).

Workup

  1. additionwas added dropwise
  2. distillationwas distilled off under vacuum
  3. customwas separated
  4. washThe organic layer was washed with 30 g of water, from which dichloromethane
  5. distillationwas distilled off under vacuum
  6. additionTo the residue was added 40 g of methyl isobutyl ketone
  7. washThis was washed with 30 g of water, with 30 g of dilute aqueous ammonia, and three times with 30 g of water whereupon methyl isobutyl ketone
  8. distillationwas distilled off under vacuum
  9. additionEther was added to the residue
  10. customdrying

Sources & evidence

ORD record
ord-0ca3418243d34130b2de1e2b33266285
Source dataset
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08057985B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes