2-Bromo-4'-(trifluoromethyl)acetophenone → 2-Thiocyanato-1-(4-trifluoromethyl-phenyl)-ethanone

HRID 1667661Notes

Reaction equation

HRID 1667661 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][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][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][CH:6]=1)=[O:4])[C:16]#[N:17]

Participants

4

Reactant 2

HCID 3219792-Bromo-4'-(trifluoromethyl)acetophenoneHCID 516872Potassium thiocyanate

Product 1

HCID 575420642-Thiocyanato-1-(4-trifluoromethyl-phenyl)-ethanoneYield 95.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 25.64 g (96.0 mmole) of 2-bromo-1-(4-trifluoromethyl-phenyl)-ethanone, 10.27 g (105.7 mmole) of potassium thiocyanate and 130 mL of ethanol (130 mL) was heated to reflux for 2 hours, and then concentrated under reduced pressure. The residue was taken up in 700 mL of ethyl acetate, washed three times with 75 mL of water, then 75 mL of brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give 22.57 g of 2-thiocyanato-1-(4-trifluoromethyl-phenyl)-ethanone as an orange-brown solid.

Workup

  1. temperatureto reflux for 2 hours
  2. concentrationconcentrated under reduced pressure
  3. washwashed three times with 75 mL of water
  4. dry with material75 mL of brine, dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-275a5f4ff45846299b617230ce112ff2
Source dataset
uspto-grants-2011_10
Patent number
US08044213B2

Reaction notes

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