Water → HCID 86612735, compound

HRID 507854Notes

Reaction equation

HRID 507854 reaction equation
[Na].[F:2][C:3]([F:21])([S:17]([OH:20])(=[O:19])=[O:18])[C:4]([O:6][CH:7]1[CH:14]2[CH2:15][CH:10]3[CH2:11][CH:12]([CH2:16][CH:8]1[CH2:9]3)[CH2:13]2)=[O:5].[Br-].[SH+:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1.O>C(#N)C>[CH:8]12[CH2:9][CH:10]3[CH2:11][CH:12]([CH2:13][CH:14]([CH2:15]3)[CH:7]1[O:6][C:4]([C:3]([F:21])([F:2])[S:17]([O-:20])(=[O:18])=[O:19])=[O:5])[CH2:16]2.[SH+:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

6

Reactant 4

HCID 962WaterHCID 5360545SodiumHCID 58021671HCID 58021671, compoundHCID 86612736HCID 86612736, compound

Product 1

HCID 86612735HCID 86612735, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.08 Parts of sodium salt of 2-adamantyl difluorosulfoacetate obtained in Example 5 (2) was dissolved in 10.8 parts of acetonitrile. To the solution, 0.93 parts of 1-oxo-2-phenylethyl)tetrahydrothiophenium bromide and 9.3 parts of ion-exchanged water were added. The added mixture was stirred for 15 hours. After the stirring, the resulting mixture was concentrated, and then the concentrate was extracted with 50 parts of chloroform twice. The organic layers were combined and then washed with ion-exchanged water. The washed organic layer was concentrated. The concentrate was washed with 30 parts of tert-butyl methyl ether and the solid deposited was collected by filtration to obtain 1.25 part of 12-oxo-2-phenylethyl)tetrahydrothiophenium (2-adamantyloxycarbonyl)difluoromethanesulfonate in the form of white solid, which is called as acid generator B6.

Workup

  1. concentrationAfter the stirring, the resulting mixture was concentrated
  2. extractionthe concentrate was extracted with 50 parts of chloroform twice
  3. washwashed with ion-exchanged water
  4. concentrationThe washed organic layer was concentrated
  5. washThe concentrate was washed with 30 parts of tert-butyl methyl ether
  6. filtrationthe solid deposited was collected by filtration

Sources & evidence

ORD record
ord-26de10b0c9044acebaf1054ab8ec82a3
Source dataset
uspto-grants-2010_08
Patent number
US07786322B2

Reaction notes

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