Diethyl Ether → 1-[6-(Trifluoromethyl)pyridin-3-yl]ethan-1-one

HRID 1678062Notes

Reaction equation

HRID 1678062 reaction equation
C[Mg+].[Br-].[F:4][C:5]([F:15])([F:14])[C:6]1[CH:13]=[CH:12][C:9](C#N)=[CH:8][N:7]=1.CC[O:18][CH2:19][CH3:20]>>[F:4][C:5]([F:15])([F:14])[C:6]1[N:7]=[CH:8][C:9]([C:19](=[O:18])[CH3:20])=[CH:12][CH:13]=1

Participants

4

Reactant 3

HCID 3283Diethyl Ether2×HCID 27775545-Cyano-2-(trifluoromethyl)pyridineHCID 178418689HCID 178418689, compound

Product 1

HCID 218805781-[6-(Trifluoromethyl)pyridin-3-yl]ethan-1-one

Procedure

A 3 M solution of MeMgBr in Et2O (7.2 mmol) was added to a stirred solution of 6-(trifluoromethyl)nicotinonitrile (0.82 g, 4.8 mmol) in ether (16 mL) dropwise over a 30 minute period. The reaction was stirred for 2 hours then the mixture was quenched with aqueous 1N HCl and extracted with Et2O. The organics were combined and washed with brine and dried over anhydrous MgSO4. The solvent was removed in vacuo yielding 530 mg of a brown solid.

Workup

  1. customthe mixture was quenched with aqueous 1N HCl
  2. extractionextracted with Et2O
  3. washwashed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-0607467a867240b985b8360d993b2414
Source dataset
uspto-grants-2011_08
Patent number
US08008487B2

Reaction notes

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