Dimethylformamide → HCID 117666967, compound

HRID 1753673Notes

Reaction equation

HRID 1753673 reaction equation
[C:1]1([S:7][C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(C)C=CC(S(O[CH2:25][C:26]([F:29])([F:28])[F:27])(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>C1(C)C=CC=CC=1.O>[F:27][C:26]([F:29])([F:28])[CH2:25][O:14][C:11]1[CH:12]=[CH:13][C:8]([S:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:9][CH:10]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 67942Ethanol, 2,2,2-trifluoro-, 1-(4-methylbenzenesulfonate)HCID 113101954-(phenylthio)phenol

Product 1

HCID 117666967HCID 117666967, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A solution was obtained by combining 20.2 g of 4-hydroxyphenyl phenyl sulfide which had been synthesized according to the well-known formulation, 15.3 g of 2,2,2-trifluoroethyl p-toluenesulfonate, 12.4 g of potassium carbonate, and 80 g of DMF. The solution was aged at 100° C. for 16 hours. The aged solution was cooled to room temperature, to which 50 g of water was added to quench the reaction. To the solution, 200 g of toluene was added for extraction. The organic layer was separated, and washed with 100 g of 5 wt % sodium hydroxide aqueous solution and water in sequence. On subsequent concentration in vacuum, 16.4 g of the target compound, phenyl 4-(2,2,2-trifluoroethoxy)phenyl sulfide was obtained as oily matter. Yield 96%.

Workup

  1. customA solution was obtained
  2. customhad been synthesized
  3. additionwas added
  4. customto quench
  5. customthe reaction
  6. customThe organic layer was separated
  7. washwashed with 100 g of 5 wt % sodium hydroxide aqueous solution and water in sequence
  8. concentrationOn subsequent concentration in vacuum, 16.4 g of the target compound

Sources & evidence

ORD record
ord-3a2268ca44da487b8d3d1dd93173045b
Source dataset
uspto-grants-2015_10
Patent number
US09164384B2

Reaction notes

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