Water → 4-n-Butanesulfonyloxyphenyl diphenylsulfonium nonafluoro-n-butanesulfonate

HRID 1351053Notes

Reaction equation

HRID 1351053 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]([F:15])([F:14])[C:4]([F:13])([F:12])[C:5]([F:11])([F:10])[S:6]([O-:9])(=[O:8])=[O:7].[OH:18][C:19]1[CH:24]=[CH:23][C:22]([S+:25]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:21][CH:20]=1.[CH2:38]([S:42](Cl)(=[O:44])=[O:43])[CH2:39][CH2:40][CH3:41].C(N(CC)CC)C.O>ClCCl>[F:17][C:2]([F:1])([F:16])[C:3]([F:14])([F:15])[C:4]([F:12])([F:13])[C:5]([F:10])([F:11])[S:6]([O-:9])(=[O:8])=[O:7].[CH2:38]([S:42]([O:18][C:19]1[CH:24]=[CH:23][C:22]([S+:25]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:21][CH:20]=1)(=[O:44])=[O:43])[CH2:39][CH2:40][CH3:41]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 754301-Butanesulfonyl chlorideHCID 22481373HCID 22481373, compound

Product 1

HCID 865967884-n-Butanesulfonyloxyphenyl diphenylsulfonium nonafluoro-n-butanesulfonateYield 73.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

30 g of 4-hydroxyphenyl diphenylsulfonium nonafluoro-n-butanesulfonate was dissolved in 300 g of dichloromethane in a reaction flask, in which the atmosphere was replaced with nitrogen. 17.9 g of n-butanesulfonyl chloride and 10.5 g of triethylamine were added in this order. The mixture was stirred for 20 minutes at room temperature. After the addition of 100 g of ion-exchanged water, the mixture was transferred to a separatory funnel, shaken, and allowed to stand still. The water layer was removed. After the addition of 300 ml of distilled water, the solution was shaken and allowed to stand still. The water layer was removed. The resulting dichloromethane solution was dried using anhydrous magnesium sulfate and filtered. After evaporating dichloromethane from the dichloromethane solution, the residual liquid was dried under reduced pressure to obtain 26.7 g of 4-n-butanesulfonyloxyphenyl diphenylsulfonium nonafluoro-n-butanesulfonate. This compound is indicated as “acid generator (A-1)”.

Workup

  1. customthe mixture was transferred to a separatory funnel
  2. stirringshaken
  3. customThe water layer was removed
  4. additionAfter the addition of 300 ml of distilled water
  5. stirringthe solution was shaken
  6. customThe water layer was removed
  7. dry with materialThe resulting dichloromethane solution was dried
  8. filtrationfiltered
  9. customAfter evaporating dichloromethane from the dichloromethane solution
  10. customthe residual liquid was dried under reduced pressure

Sources & evidence

ORD record
ord-bf06902f67be405c9d048e256c4a904b
Source dataset
uspto-grants-2007_05
Patent number
US07217492B2

Reaction notes

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