(4-Octyloxyphenyl)phenyliodonium tosylate → (4-Octyloxyphenyl)-phenyliodonium tetrakis(pentafluorophenyl)borate

HRID 1859095Notes

Reaction equation

HRID 1859095 reaction equation
S(C1C=CC(C)=CC=1)([O-])(=O)=O.[CH2:12]([O:20][C:21]1[CH:26]=[CH:25][C:24]([I+:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:23][CH:22]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].[F:34][C:35]1[C:40]([B-:41]([C:64]2[C:69]([F:70])=[C:68]([F:71])[C:67]([F:72])=[C:66]([F:73])[C:65]=2[F:74])([C:53]2[C:58]([F:59])=[C:57]([F:60])[C:56]([F:61])=[C:55]([F:62])[C:54]=2[F:63])[C:42]2[C:47]([F:48])=[C:46]([F:49])[C:45]([F:50])=[C:44]([F:51])[C:43]=2[F:52])=[C:39]([F:75])[C:38]([F:76])=[C:37]([F:77])[C:36]=1[F:78].[Li+]>CC(C)=O>[F:70][C:69]1[C:64]([B-:41]([C:42]2[C:47]([F:48])=[C:46]([F:49])[C:45]([F:50])=[C:44]([F:51])[C:43]=2[F:52])([C:40]2[C:39]([F:75])=[C:38]([F:76])[C:37]([F:77])=[C:36]([F:78])[C:35]=2[F:34])[C:53]2[C:54]([F:63])=[C:55]([F:62])[C:56]([F:61])=[C:57]([F:60])[C:58]=2[F:59])=[C:65]([F:74])[C:66]([F:73])=[C:67]([F:72])[C:68]=1[F:71].[CH2:12]([O:20][C:21]1[CH:22]=[CH:23][C:24]([I+:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:25][CH:26]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

4

Reactant 2

HCID 22131423(4-Octyloxyphenyl)phenyliodonium tosylateHCID 23709652Lithium tetrakis(pentafluorophenyl)borate

Product 1

HCID 11040449(4-Octyloxyphenyl)-phenyliodonium tetrakis(pentafluorophenyl)borateYield 92%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

5 g (or 0.0086 mol) of (4-octyloxyphenyl)phenyliodonium tosylate were dissolved in 350 ml of acetone in a 500 ml Erlenmeyer flask equipped with a magnetic stirrer bar. While light was excluded, 3.4 g (or 0.0103 mol) of lithium tetrakis(pentafluorophenyl)borate in solution in 50 ml of acetone were added. The mixture was stirred for 48 hours and was then filtered to remove the lithium p-toluenesulfonate formed. The acetone was evaporated under reduced pressure and 7.98 g (or a yield of 92%) of ((4-octyloxyphenyl)phenyliodonium tetrakis(pentafluorophenyl)borate were recovered.

Workup

  1. customequipped with a magnetic stirrer bar
  2. filtrationwas then filtered
  3. customto remove the lithium p-toluenesulfonate
  4. customformed
  5. customThe acetone was evaporated under reduced pressure and 7.98 g (or a yield of 92%) of ((4-octyloxyphenyl)phenyliodonium tetrakis(pentafluorophenyl)borate
  6. customwere recovered

Sources & evidence

ORD record
ord-923e5fc615b84bc5856077d26c634622
Source dataset
uspto-grants-2000_11
Patent number
US06153661

Reaction notes

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