Water → HCID 59596840, compound

HRID 1092395Notes

Reaction equation

HRID 1092395 reaction equation
[C-:1]#[N:2].[K+].Br[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[C:8]([O:13][CH2:14][C:15]([F:18])([F:17])[F:16])[CH:7]=1.O>CS(C)=O>[F:12][C:9]1[CH:10]=[CH:11][C:6]([CH2:5][C:1]#[N:2])=[CH:7][C:8]=1[O:13][CH2:14][C:15]([F:18])([F:17])[F:16]

Participants

5

Reactant 3

HCID 962WaterHCID 9032Potassium CyanideHCID 59596843HCID 59596843, compound

Product 1

HCID 59596840HCID 59596840, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

900 mg (13.8 mmol) of KCN were added to a solution of 3.3 g (11.5 mmol) of 4-bromomethyl-1-fluoro-2-(2,2,2-trifluoro-ethoxy)-benzene in 30 ml of dry dimethylsulfoxide. The reaction mixture was stirred for 1 hour at room temperature. Water was added and the product was extracted with diethyl ether. The solvent was removed under vacuum and the crude residue was purified by flash chromatography (hexane/ethyl acetate 8:2 v:v). 1.4 g (52% yield) of the title compound were isolated as a white solid.

Workup

  1. extractionthe product was extracted with diethyl ether
  2. customThe solvent was removed under vacuum
  3. customthe crude residue was purified by flash chromatography (hexane/ethyl acetate 8:2 v:v)

Sources & evidence

ORD record
ord-28c5e4b89d5b4fd28d6e942101ccf39a
Source dataset
uspto-grants-2012_03
Patent number
US08129427B2

Reaction notes

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