Triphenylphosphine → 2-(4-Trifluoromethylphenyl)ethyl-[2,4-dichloro-5-(2,2,2-trifluoroethylsulfinyl)phenyl] ether

HRID 522451Notes

Reaction equation

HRID 522451 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([S:9]([CH2:11][C:12]([F:15])([F:14])[F:13])=[O:10])=[CH:4][C:3]=1[OH:16].[F:17][C:18]([F:29])([F:28])[C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26]O)=[CH:21][CH:20]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1.C(OCC)(=O)C.CCCCCC>[F:17][C:18]([F:28])([F:29])[C:19]1[CH:20]=[CH:21][C:22]([CH2:25][CH2:26][O:16][C:3]2[CH:4]=[C:5]([S:9]([CH2:11][C:12]([F:13])([F:15])[F:14])=[O:10])[C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])=[CH:23][CH:24]=1

Participants

8

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 112755102-(4-(Trifluoromethyl)phenyl)ethan-1-olHCID 1178996892,4-Dichloro-5-(2,2,2-trifluoroethylsulfinyl)phenol

Product 1

HCID 1178997452-(4-Trifluoromethylphenyl)ethyl-[2,4-dichloro-5-(2,2,2-trifluoroethylsulfinyl)phenyl] etherYield 52%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

In 30 ml of tetrahydrofuran were dissolved 0.5 g (1.71 mmol) of 2,4-dichloro-5-(2,2,2-trifluoroethylsulfinyl)phenol, 0.33 g (1.74 mmol) of 2-(4-trifluoromethylphenyl)ethanol and 0.49 g (1.87 mmol) of triphenylphosphine. Thereto was added 0.38 g (1.87 mmol) of diisopropyl azodicarboxylate at room temperature, and the reaction mixture was stirred for 16 hours. Then, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent: a mixed solvent of n-hexane:ethyl acetate=5:1), to obtain 0.41 g (yield: 52%) of an intended product.

Workup

  1. distillationThen, the solvent was distilled off under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (

Sources & evidence

ORD record
ord-086c33e73a7442718abacb30a35666ab
Source dataset
uspto-grants-2016_05
Patent number
US09332754B2

Reaction notes

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