2-(3-Cyano-4-fluorophenyl)acetic acid → HCID 45925946, compound

HRID 1810094Notes

Reaction equation

HRID 1810094 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH2:10][C:11]([OH:13])=[O:12])[CH:6]=[CH:7][C:8]=1[F:9])#[N:2]>C1COCC1>[C:1]([C:3]1[CH:4]=[C:5]([CH2:10][C:11]([O:13][C:3]([CH3:4])([CH3:8])[CH3:1])=[O:12])[CH:6]=[CH:7][C:8]=1[F:9])#[N:2]

Participants

3

Reactant 1

HCID 27739352-(3-Cyano-4-fluorophenyl)acetic acid

Product 1

HCID 45925946HCID 45925946, compoundYield 106.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(3-Cyano-4-fluorophenyl)acetic acid (14.3 g, 79.8 mmol) was diluted with THF (150 mL) followed by the addition of tert-butyl N,N′-diispropylcarbamimidate (48.0 g, 239 mmol). After stirring for 12 hours, the reaction was filtered and the filtrate was concentrated. The residue was taken up in ethyl acetate 100 mL and washed with 1N HCl saturated bicarbonate water and brine. The organic layer was dried over MgSO4, filtered and concentrated. Additional precipitate was removed by filtration. The remaining residue was purified on a Biotage 40M column eluting over silica gel with hexanes:ethyl acetate (9:1) to yield tert-butyl 2-(3-cyano-4-fluorophenyl)acetate (10.0 g, 53.3% yield) as a clear oil that later solidified to a white solid.

Workup

  1. additionfollowed by the addition of tert-butyl N,N′-diispropylcarbamimidate (48.0 g, 239 mmol)
  2. filtrationthe reaction was filtered
  3. concentrationthe filtrate was concentrated
  4. washwashed with 1N HCl saturated bicarbonate water and brine
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customAdditional precipitate was removed by filtration
  9. customThe remaining residue was purified on a Biotage 40M column
  10. washeluting over silica gel with hexanes:ethyl acetate (9:1)

Sources & evidence

ORD record
ord-2e2b92044ce44ec58402f59b1b2da079
Source dataset
uspto-grants-2013_01
Patent number
US08362056B2

Reaction notes

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