Water → HCID 86644963, compound

HRID 2091442Notes

Reaction equation

HRID 2091442 reaction equation
[C:1]12([CH2:11][C:12]([F:18])([F:17])[S:13]([O-:16])(=[O:15])=[O:14])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[Na+].[Br-].[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.O>ClCCl>[C:1]12([CH2:11][C:12]([F:18])([F:17])[S:13]([O-:16])(=[O:14])=[O:15])[CH2:10][CH:5]3[CH2:4][CH:3]([CH2:9][CH:7]([CH2:6]3)[CH2:8]1)[CH2:2]2.[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

5

Reactant 3

HCID 962WaterHCID 11984010Triphenylsulfonium BromideHCID 59471130HCID 59471130, compound

Product 1

HCID 86644963HCID 86644963, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A reaction flask was charged with 53.2 g of sodium 2-(adamantan-1-yl)-1,1-difluoroethane-1-sulfonate and 54.9 g of triphenylsulfonium bromide. After the addition of 500 ml of ion-exchanged water and 500 ml of dichloromethane, the mixture was stirred at room temperature for one hour. The organic layer was separated, and washed five times with 500 ml of ion-exchanged water. The solvent was then removed to obtain 78.1 g of triphenylsulfonium 2-(adamantan-1-yl)-1,1-difluoroethane-1-sulfonate. The resulting triphenylsulfonium 2-(adamantan-1-yl)-1,1-difluoroethane-1-sulfonate was analyzed by 1H-NMR (“JNM-EX270” manufactured by JEOL Ltd.) (solvent: deuterated water). The chemical shift was 1H-NMR [σ ppm (D2O): 1.64-1.76 (12H, m), 1.92-2.10 (5H, m), 7.76-7.89 (15H, m)] and 19F-NMR [σ ppm (DMSO-d6): 58.82 (m)] (the peak of sodium 3-trimethylsilylpropionate-2-2,2,3,3-d4 (1H-NMR) or the peak of hexafluorobenzene (19F-NMR) was determined to be 0 ppm). This indicates that the target compound was obtained. The purity was 99 wt % or higher.

Workup

  1. customThe organic layer was separated
  2. washwashed five times with 500 ml of ion-exchanged water
  3. customThe solvent was then removed

Sources & evidence

ORD record
ord-9b9a8c31c2b54a299fc20c6b52a82b05
Source dataset
uspto-grants-2013_05
Patent number
US08440384B2

Reaction notes

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