4-Methylbenzenethiol → HCID 57656218, compound

HRID 911450Notes

Reaction equation

HRID 911450 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.[H-].[Na+].[F:11][C:12]([F:26])([F:25])[C:13]([CH3:24])([C:20]([F:23])([F:22])[F:21])[CH2:14]OS(C)(=O)=O>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:14][C:13]([CH3:24])([C:12]([F:11])([F:25])[F:26])[C:20]([F:23])([F:22])[F:21])=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 78114-MethylbenzenethiolHCID 24758Sodium hydrideHCID 86661654HCID 86661654, compound

Product 1

HCID 57656218HCID 57656218, compoundYield 66.2%

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
150 °C

Procedure

In a sealed tube dissolve 4-methylbenzenethiol (4.13 g, 33.2 mmol) in DMF (20 mL) at ambient temperature. Add portionwise with stirring sodium hydride (899 mg, 37.5 mmol) followed by tetrabutylammonium iodide (82 mg, 0.22 mmol) and a solution of methanesulfonic acid 3,3,3-trifluoro-2-methyl-2-trifluoromethylpropyl ester (6.16 g, 22.5 mmol) in DMF (10 mL). Stir at 150° C. overnight, cool the mixture to ambient temperature and dilute cautiously with water. Extract three times with EtOAc, dry over anhydrous Na2SO4, and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane to give the desired intermediate as a yellow oil (4.5 g, 62%).

Workup

  1. temperaturecool the mixture to ambient temperature
  2. extractionExtract three times with EtOAc
  3. dry with materialdry over anhydrous Na2SO4
  4. concentrationconcentrate in vacuo
  5. customPurify by chromatography on silica gel eluting with hexane

Sources & evidence

ORD record
ord-908321f374164cec9919083246ae1c8f
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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