Water → 2-Fluoro-5-formylbenzonitrile

HRID 895293Notes

Reaction equation

HRID 895293 reaction equation
C([Mg]Br)(C)C.Br[C:7]1[CH:8]=[CH:9][C:10]([F:15])=[C:11]([CH:14]=1)[C:12]#[N:13].CN(C)[CH:18]=[O:19].O>O1CCCC1>[F:15][C:10]1[CH:9]=[CH:8][C:7]([CH:18]=[O:19])=[CH:14][C:11]=1[C:12]#[N:13]

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 27249005-Bromo-2-fluorobenzonitrileHCID 178418365HCID 178418365, compound

Product 1

HCID 27695822-Fluoro-5-formylbenzonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Iso-propyl magnesium bromide (18 ml, 1M in tetrahydrofuran, 18 mmol) was added dropwise to an ice-cooled solution of 5-bromo-2-fluorobenzonitrile (3 g, 15.1 mmol) in tetrahydrofuran (25 ml), and once addition was complete, the mixture was allowed to warm to room temperature and stirred for a further 2 hours. N,N-Dimethylformamide (3.5 ml, 45.2 mmol) was added and the reaction stirred for 3 hours. Water was added and the mixture extracted with ethyl acetate (3×). The combined organic extracts were washed with 6% aqueous magnesium sulphate solution, and brine, then dried (Na2SO4) and concentrated under reduced pressure. The product was purified by column chromatography on silica gel using an elution gradient of ethyl acetate:hexane (10:90 to 20:80) to afford the title compound as a light yellow solid, 1.01 g.

Workup

  1. temperaturecooled
  2. stirringthe reaction stirred for 3 hours
  3. extractionthe mixture extracted with ethyl acetate (3×)
  4. washThe combined organic extracts were washed with 6% aqueous magnesium sulphate solution, and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe product was purified by column chromatography on silica gel using an elution gradient of ethyl acetate:hexane (10:90 to 20:80)

Sources & evidence

ORD record
ord-22c5f7fffea3451aae328618c31f1af2
Source dataset
uspto-grants-2005_07
Patent number
US06914160B1

Reaction notes

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