Diethyl Ether → 3-Trifluoromethylphenylthioacetonitrile

HRID 612990Notes

Reaction equation

HRID 612990 reaction equation
[Na].[F:2][C:3]([F:12])([F:11])[C:4]1[CH:5]=[C:6]([SH:10])[CH:7]=[CH:8][CH:9]=1.Cl[CH2:14][C:15]#[N:16].CCOCC>C(O)C>[F:12][C:3]([F:2])([F:11])[C:4]1[CH:5]=[C:6]([S:10][CH2:14][C:15]#[N:16])[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 7856ChloroacetonitrileHCID 1367513-(Trifluoromethyl)benzenethiolHCID 5360545Sodium

Product 1

HCID 185438013-Trifluoromethylphenylthioacetonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To sodium (0.62 g, 27.0 mmol) dissolved in 40 mL of ethanol was added 4.79 g (26.9 mmol) of 3-trifluoromethylthiophenol and 2.04 g (27.0 mmol) of chloroacetonitrile. The reaction mixture was heated at reflux for 1 hour and then stirred overnight at room temperature. To the cooled reaction mixture was added one volume of ether and the precipitated solids were removed by filtration. The filtrate was evaporated on the rotary evaporator to give the product as an oil in essentially quantitative yield. This material was used in the following reaction without further purification.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 1 hour
  3. customTo the cooled reaction mixture
  4. customthe precipitated solids were removed by filtration
  5. customThe filtrate was evaporated on the rotary evaporator

Sources & evidence

ORD record
ord-aa62c2f81f7b4bba8b726abe0869c232
Source dataset
uspto-grants-1999_12
Patent number
US06005109

Reaction notes

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