Dimethyl Sulfoxide → HCID 23124062, compound

HRID 1452995Notes

Reaction equation

HRID 1452995 reaction equation
CS(C)=O.FC(F)(F)S(O[C:11]1[CH:32]=[CH:31][CH:30]=[CH:29][C:12]=1[C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1OS(C(F)(F)F)(=O)=O)=[O:14])(=O)=O.[C:35]1([PH:41](=[O:48])[C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.C(N(CC)[CH:53]([CH3:55])[CH3:54])(C)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)CCCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CO.C(Cl)Cl>[C:35]1([P:41]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)([C:11]2[CH:32]=[CH:31][CH:30]=[CH:29][C:12]=2[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[P:41]([C:54]2[CH:53]=[CH:55][CH:47]=[CH:42][CH:43]=2)([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[O:48])=[O:14])=[O:48])[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

9

Reactant 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 254003Diphenylphosphine oxideHCID 16082223HCID 16082223, compound

Product 1

HCID 23124062HCID 23124062, compoundYield 108.1%

Reagents, catalysts & solvents 4

HCID 821241,4-Bis(diphenylphosphino)butaneCatalystHCID 167845palladium(II) acetateCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Into 5 ml of dimethylsulfoxide were dissolved 191.3 mg (0.4 mmol) of 2,2′-bis(trifluoromethanesulfonyloxy)benzophenone, 9.0 mg (0.04 mmol) of palladium acetate, 17.0 mg (0.04 mmol) of 1,4-bis(diphenylphosphino)butane, and 310 mg (1.2 mmol) of diphenylphosphine oxide, and further thereto was added 191.3 mg (0.4 mmol) of N,N-diisopropylethylamine. The resultant solution was stirred at 100° C. for 18 hours. The reaction mixture was cooled to room temperature, and 10 ml of methylene chloride was added thereto. This solution was washed with 1 N hydrochloric acid, water and brine in sequence, and then dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and then the resultant was purified by column chromatography on silica gel (ethyl acetate-methylene chloride:methanol=10:1 to give 252 mg (yield: 90%) of the title compound in the form of a brownish-red solid.

Workup

  1. washThis solution was washed with 1 N hydrochloric acid, water and brine in sequence
  2. dry with materialdried over magnesium sulfate
  3. distillationThe solvent was distilled off under reduced pressure
  4. customthe resultant was purified by column chromatography on silica gel (ethyl acetate-methylene chloride

Sources & evidence

ORD record
ord-566218ad5f874a379f8bd17af4711ed0
Source dataset
uspto-grants-2009_01
Patent number
US07473793B2

Reaction notes

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