Tributylstannane → 1254114-69-6

HRID 1755037Notes

Reaction equation

HRID 1755037 reaction equation
[CH3:1][O:2][C:3](=[O:25])[C:4]1[CH:9]=[CH:8][C:7]([CH:10](OC(OC2C=CC=CC=2)=S)[C:11]([F:14])([F:13])[F:12])=[CH:6][CH:5]=1.CC(N=NC(C#N)(C)C)(C#N)C.C([SnH](CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:25])[C:4]1[CH:5]=[CH:6][C:7]([CH2:10][C:11]([F:13])([F:12])[F:14])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 86672779HCID 86672779, compound

Product 1

HCID 601956831254114-69-6Yield 93.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

4-(2,2,2-Trifluoro-1-phenoxythiocarbonyloxy-ethyl)-benzoic acid methyl ester (462.8 mg, 1.25 mmol) and AIBN (41.0 mg, 0.25 mmol) were dissolved in ultrasonically degassed toluene (12.5 mL). Tri-n-butyltin hydride (0.50 mL, 1.874 mmol) was added and the mixture was heated with stirring at 80° C. for two hours. The reaction solution was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography to give 4-(2,2,2-trifluoro-ethyl)-benzoic acid methyl ester as white crystals (254.6 mg, 93%).

Workup

  1. temperaturethe mixture was heated
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. customthe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-34f478f3bd4c46b6a3e717ad39bcec87
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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