Potassium thiocyanate → 2-Oxo-2-[3-(trifluoromethyl)phenyl]ethyl thiocyanate

HRID 1667669Notes

Reaction equation

HRID 1667669 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:14])([F:13])[F:12])[CH:6]=1)=[O:4].[S-:15][C:16]#[N:17].[K+]>C(O)C>[S:15]([CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:14])([F:13])[F:12])[CH:6]=1)=[O:4])[C:16]#[N:17]

Participants

4

Reactant 2

HCID 516872Potassium thiocyanateHCID 27783862-Bromo-1-[3-(trifluoromethyl)phenyl]ethan-1-one

Product 1

HCID 862452532-Oxo-2-[3-(trifluoromethyl)phenyl]ethyl thiocyanateYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 10.17 g (36.83 mmole) of 2-bromo-1-(3-trifluoromethyl-phenyl)-ethanone, 4.07 g (41.98 mmole) of potassium thiocyanate and ethanol was heated at reflux for 2 hours. The cooled mixture was concentrated under reduced pressure. The residue was taken up in 225 mL of ethyl acetate, washed three times with 50 mL of water, then 50 mL of brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give 8.85 g of 2-thiocyanato-1-(3-trifluoromethyl-phenyl)-ethanone.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. concentrationThe cooled mixture was concentrated under reduced pressure
  4. washwashed three times with 50 mL of water
  5. dry with material50 mL of brine, dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-466333d98a5a42f2bc4e140cf90f86fd
Source dataset
uspto-grants-2011_10
Patent number
US08044213B2

Reaction notes

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