Water → HCID 131719334, compound

HRID 1440930Notes

Reaction equation

HRID 1440930 reaction equation
[CH2:1]([B-:4]([C:19]1[CH:24]=[CH:23][C:22]([Br:25])=[CH:21][CH:20]=1)([C:12]1[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][CH:13]=1)[C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][CH:6]=1)[CH:2]=[CH2:3].[Li+].F[Sb-](F)(F)(F)(F)F.[C:34]1([S+:40]([C:52]2[C:61]3[C:56](=[CH:57][CH:58]=[CH:59][CH:60]=3)[CH:55]=[CH:54][CH:53]=2)[CH2:41][C:42]2[C:51]3[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=3)[CH:45]=[CH:44][CH:43]=2)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.O>C(#N)C.CC(C)=O>[CH2:1]([B-:4]([C:12]1[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][CH:13]=1)([C:19]1[CH:24]=[CH:23][C:22]([Br:25])=[CH:21][CH:20]=1)[C:5]1[CH:6]=[CH:7][C:8]([Br:11])=[CH:9][CH:10]=1)[CH:2]=[CH2:3].[C:34]1([S+:40]([C:52]2[C:61]3[C:56](=[CH:57][CH:58]=[CH:59][CH:60]=3)[CH:55]=[CH:54][CH:53]=2)[CH2:41][C:42]2[C:51]3[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=3)[CH:45]=[CH:44][CH:43]=2)[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

6

Reactant 3

HCID 962WaterHCID 88398166HCID 88398166, compoundHCID 131719336HCID 131719336, compound

Product 1

HCID 131719334HCID 131719334, compoundYield 34.4%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 4.30 g of lithium allyltris(p-bromophenyl)borate in 50 ml of acetonitrile was added to a solution of 5.00 g of phenyl (1-naphthyl) (1-naphthylmethyl)sulfonium hexafluoroantimonate in 100 ml of acetone, and the resultant mixture was stirred at room temperature for 30 minutes. Then, 200 ml of water was added. The resultant precipitate of a yellow oily component was recovered, and 100 ml of dichloromethane was added. The dichloromethane layer was washed with water, dried and concentrated to give 2.52 g of phenyl(1-naphthyl)(1-naphthylmethyl) sulfonium-allyltris(p-bromophenyl)borate.

Workup

  1. customThe resultant precipitate of a yellow oily component was recovered
  2. addition100 ml of dichloromethane was added
  3. washThe dichloromethane layer was washed with water
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-cd30a14370e543398fc95a4713f49771
Source dataset
uspto-grants-1996_03
Patent number
US05500453

Reaction notes

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